WO1988000592A1 - SYNTHESE DIASTEREOSELECTIVE DE STRECKER D'ACIDES AMINES alpha A PARTIR DE DERIVES DE GLYCOSYLAMINE - Google Patents
SYNTHESE DIASTEREOSELECTIVE DE STRECKER D'ACIDES AMINES alpha A PARTIR DE DERIVES DE GLYCOSYLAMINE Download PDFInfo
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- WO1988000592A1 WO1988000592A1 PCT/EP1987/000371 EP8700371W WO8800592A1 WO 1988000592 A1 WO1988000592 A1 WO 1988000592A1 EP 8700371 W EP8700371 W EP 8700371W WO 8800592 A1 WO8800592 A1 WO 8800592A1
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- 238000007059 Strecker synthesis reaction Methods 0.000 title claims abstract description 10
- 229930182474 N-glycoside Natural products 0.000 title abstract description 9
- 150000002341 glycosylamines Chemical class 0.000 title abstract description 9
- 150000001371 alpha-amino acids Chemical class 0.000 title description 3
- 235000008206 alpha-amino acids Nutrition 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 26
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 20
- -1 (1) Chemical class 0.000 claims abstract description 19
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 15
- 238000002360 preparation method Methods 0.000 claims abstract description 5
- 150000001412 amines Chemical class 0.000 claims abstract description 4
- 238000006243 chemical reaction Methods 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 10
- 125000002252 acyl group Chemical group 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 150000001720 carbohydrates Chemical group 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000006239 protecting group Chemical group 0.000 claims description 4
- 229910052717 sulfur Chemical group 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 230000009467 reduction Effects 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000001488 beta-D-galactosyl group Chemical group C1([C@H](O)[C@@H](O)[C@@H](O)[C@H](O1)CO)* 0.000 claims description 2
- 235000014633 carbohydrates Nutrition 0.000 claims description 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 150000002402 hexoses Chemical class 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- ORTFAQDWJHRMNX-UHFFFAOYSA-M oxidooxomethyl Chemical compound [O-][C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-M 0.000 claims description 2
- 150000002972 pentoses Chemical class 0.000 claims description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
- 239000011593 sulfur Chemical group 0.000 claims description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 1
- 239000002904 solvent Substances 0.000 abstract description 9
- 230000006698 induction Effects 0.000 abstract description 7
- 239000002841 Lewis acid Substances 0.000 abstract description 2
- 239000011968 lewis acid catalyst Substances 0.000 abstract description 2
- 150000007517 lewis acids Chemical class 0.000 abstract description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 17
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 15
- FJJYHTVHBVXEEQ-UHFFFAOYSA-N 2,2-dimethylpropanal Chemical compound CC(C)(C)C=O FJJYHTVHBVXEEQ-UHFFFAOYSA-N 0.000 description 10
- 238000004128 high performance liquid chromatography Methods 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- IPRZVEFFDTWBGV-DISONHOPSA-N [(2r,3s,4s,5r,6r)-6-amino-3,4,5-tris(2,2-dimethylpropanoyloxy)oxan-2-yl]methyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OC[C@H]1O[C@@H](N)[C@H](OC(=O)C(C)(C)C)[C@@H](OC(=O)C(C)(C)C)[C@H]1OC(=O)C(C)(C)C IPRZVEFFDTWBGV-DISONHOPSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 230000014759 maintenance of location Effects 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- WCWOEQFAYSXBRK-SVZMEOIVSA-N (3r,4s,5r,6r)-2-amino-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound NC1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O WCWOEQFAYSXBRK-SVZMEOIVSA-N 0.000 description 4
- BXRFQSNOROATLV-UHFFFAOYSA-N 4-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=C(C=O)C=C1 BXRFQSNOROATLV-UHFFFAOYSA-N 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 235000001014 amino acid Nutrition 0.000 description 4
- 150000001413 amino acids Chemical class 0.000 description 4
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- CNUDBTRUORMMPA-UHFFFAOYSA-N formylthiophene Chemical compound O=CC1=CC=CS1 CNUDBTRUORMMPA-UHFFFAOYSA-N 0.000 description 4
- LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- FAGLEPBREOXSAC-UHFFFAOYSA-N tert-butyl isocyanide Chemical compound CC(C)(C)[N+]#[C-] FAGLEPBREOXSAC-UHFFFAOYSA-N 0.000 description 3
- WQZGKKKJIJFFOK-SVZMEOIVSA-N (+)-Galactose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-SVZMEOIVSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 239000000411 inducer Substances 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 2
- 235000005074 zinc chloride Nutrition 0.000 description 2
- 239000011592 zinc chloride Substances 0.000 description 2
- NPDBDJFLKKQMCM-BYPYZUCNSA-N (2r)-2-azaniumyl-3,3-dimethylbutanoate Chemical class CC(C)(C)[C@@H]([NH3+])C([O-])=O NPDBDJFLKKQMCM-BYPYZUCNSA-N 0.000 description 1
- NPDBDJFLKKQMCM-SCSAIBSYSA-N (2s)-2-amino-3,3-dimethylbutanoic acid Chemical class CC(C)(C)[C@H](N)C(O)=O NPDBDJFLKKQMCM-SCSAIBSYSA-N 0.000 description 1
- RQBSUMJKSOSGJJ-HWQSCIPKSA-N (3R,4S,5S)-2-aminooxane-3,4,5-triol Chemical class NC1OC[C@H](O)[C@H](O)[C@H]1O RQBSUMJKSOSGJJ-HWQSCIPKSA-N 0.000 description 1
- WCWOEQFAYSXBRK-GASJEMHNSA-N (3r,4s,5s,6r)-2-amino-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound NC1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O WCWOEQFAYSXBRK-GASJEMHNSA-N 0.000 description 1
- RNHDAKUGFHSZEV-UHFFFAOYSA-N 1,4-dioxane;hydrate Chemical compound O.C1COCCO1 RNHDAKUGFHSZEV-UHFFFAOYSA-N 0.000 description 1
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 1
- XCVDAQWKJUCVHJ-UHFFFAOYSA-N 2-azaniumyl-2-(4-nitrophenyl)acetate Chemical class OC(=O)C(N)C1=CC=C([N+]([O-])=O)C=C1 XCVDAQWKJUCVHJ-UHFFFAOYSA-N 0.000 description 1
- SRWILAKSARHZPR-UHFFFAOYSA-N 3-chlorobenzaldehyde Chemical compound ClC1=CC=CC(C=O)=C1 SRWILAKSARHZPR-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- WSNMPAVSZJSIMT-UHFFFAOYSA-N COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 Chemical compound COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 WSNMPAVSZJSIMT-UHFFFAOYSA-N 0.000 description 1
- ZGUNAGUHMKGQNY-SSDOTTSWSA-N D-alpha-phenylglycine Chemical compound OC(=O)[C@H](N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-SSDOTTSWSA-N 0.000 description 1
- 108010016626 Dipeptides Proteins 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 description 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 239000002262 Schiff base Substances 0.000 description 1
- 150000004753 Schiff bases Chemical class 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000006058 Ugi-reaction Methods 0.000 description 1
- IPRZVEFFDTWBGV-ZBRFXRBCSA-N [(2r,3r,4s,5s,6s)-6-amino-3,4,5-tris(2,2-dimethylpropanoyloxy)oxan-2-yl]methyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OC[C@H]1O[C@H](N)[C@@H](OC(=O)C(C)(C)C)[C@@H](OC(=O)C(C)(C)C)[C@@H]1OC(=O)C(C)(C)C IPRZVEFFDTWBGV-ZBRFXRBCSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000001370 alpha-amino acid derivatives Chemical class 0.000 description 1
- 125000000089 arabinosyl group Chemical group C1([C@@H](O)[C@H](O)[C@H](O)CO1)* 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000006345 epimerization reaction Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000002519 galactosyl group Chemical group C1([C@H](O)[C@@H](O)[C@@H](O)[C@H](O1)CO)* 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 1
- 150000002340 glycosyl compounds Chemical class 0.000 description 1
- 125000003147 glycosyl group Chemical group 0.000 description 1
- 150000002390 heteroarenes Chemical class 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000000311 mannosyl group Chemical group C1([C@@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- SEDZOYHHAIAQIW-UHFFFAOYSA-N trimethylsilyl azide Chemical compound C[Si](C)(C)N=[N+]=[N-] SEDZOYHHAIAQIW-UHFFFAOYSA-N 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
Definitions
- Dias teredm ere pure It can be isolated in a yield of approximately 65%.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
L'invention concerne des glycosylamines à O-acyl protégé, en particulier 2,3,4,6-tétra-O-pivaloyl-beta-D-galactopyranosylamine (1), leur préparation et leur utilisation pour la synthèse diastéréosélective d'acides aminés alpha. On peut obtenir par synthèse de Strecker avec des composés tels que (1) des rendements et des excédents élevés de diastéréomères, le sens de l'induction asymétrique pouvant être déterminé par le choix du solvant. Ce type de synthèse est particulièrement efficace lorsqu'il est effectué en présence d'acides de Lewis catalyseurs. En utilisant des amines telles que (1), on peut également obtenir des rendements élevés et une bonne diastéréosélectivité pendant des procédés de synthèse à quatre composantes selon Ugi facilités par des acides de Lewis.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62504526A JPH03501966A (ja) | 1987-07-10 | 1987-07-10 | グリコシルアミンとそのＮ‐アルキリデン誘導体；その製造法と特にα‐アミノ酸とその誘導体のジアステレオ選択合成におけるその使用 |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19863624376 DE3624376A1 (de) | 1986-07-18 | 1986-07-18 | Glycosylamine und deren n-alkyliden-derivate |
| DEP3624376.0 | 1986-07-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1988000592A1 true WO1988000592A1 (fr) | 1988-01-28 |
Family
ID=6305504
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP1987/000371 WO1988000592A1 (fr) | 1986-07-18 | 1987-07-10 | SYNTHESE DIASTEREOSELECTIVE DE STRECKER D'ACIDES AMINES alpha A PARTIR DE DERIVES DE GLYCOSYLAMINE |
Country Status (3)
| Country | Link |
|---|---|
| EP (1) | EP0274515A1 (fr) |
| DE (1) | DE3624376A1 (fr) |
| WO (1) | WO1988000592A1 (fr) |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1994015941A1 (fr) * | 1993-01-14 | 1994-07-21 | Akzo N.V. | α-AMINONITRILES DERIVES D'UN SUCRE AMINE |
| FR2721612A1 (fr) * | 1994-06-23 | 1995-12-29 | Idm | Nouveaux dérivés d'oligosides, leur procédé de préparation et leurs applications. |
| WO2003006474A3 (fr) * | 2001-07-11 | 2003-05-01 | Schering Ag | Procede de production de 1-o-glycosides peracyles |
| US6831164B2 (en) | 2001-07-11 | 2004-12-14 | Schering Aktiengesellschaft | Process for the production of peracylated 1-0-glycosides |
| CN1300090C (zh) * | 2005-03-02 | 2007-02-14 | 杭州师范学院 | 一种芳基乙酸的制备方法 |
| US8967361B2 (en) | 2013-02-27 | 2015-03-03 | Outerwall Inc. | Coin counting and sorting machines |
| US9022841B2 (en) | 2013-05-08 | 2015-05-05 | Outerwall Inc. | Coin counting and/or sorting machines and associated systems and methods |
| US9036890B2 (en) | 2012-06-05 | 2015-05-19 | Outerwall Inc. | Optical coin discrimination systems and methods for use with consumer-operated kiosks and the like |
| US9443367B2 (en) | 2014-01-17 | 2016-09-13 | Outerwall Inc. | Digital image coin discrimination for use with consumer-operated kiosks and the like |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5292918A (en) * | 1990-04-26 | 1994-03-08 | Schering Corporation | Diastereoselective process for preparing n-substituted amino acids and derivatives |
| WO2000043352A1 (fr) * | 1999-01-22 | 2000-07-27 | Pharmacore, Inc. | Methode permettant de synthetiser des composes de formule 1 et leurs derives |
-
1986
- 1986-07-18 DE DE19863624376 patent/DE3624376A1/de not_active Withdrawn
-
1987
- 1987-07-10 EP EP19870904863 patent/EP0274515A1/fr not_active Withdrawn
- 1987-07-10 WO PCT/EP1987/000371 patent/WO1988000592A1/fr not_active Application Discontinuation
Non-Patent Citations (8)
| Title |
|---|
| Angewandte Chemie, International Edition in English, Band 24, 1985, VCH Verlagsgesellschaft mbH, (Weinheim, DE), L.F. TIETZE et al.: "Synthesis of 1,4- Dihydropyridine Nucleosides by Photochemical Cycloaddition", seiten 127-128 siehe seite 128, verbindungen 3A-C * |
| Angewandte Chemie, International Edition in English, Band 26, Nr. 1987, VCH Verlagsgesellschaft mbH, (Weinheim, DE), H. KUNZ et al.: "Diasteroselective Strecker Synthesis of alfa-Aminonitriles on Carbohydrate Templates", seiten 557-559 siehe das ganze dokument * |
| CHEMICAL ABSTRACTS, Chemical Substance Index, Band 102, Teil 3, Januar-Juni 1985, (Columbus, Ohio, US), siehe seite 3471, beta-D-Glucopyranosylamine -,N-((4-Bromophenyl)Methylene)-2,3,4,6- Tetraacetate -,N-((4-Chlorophenyl)Methylene) -2,3,4,6- Tetraacetate -,N-((4-Methoxyphenyl)Methylene)-2,3,4,6- Tetraacetate -,N-((4-Nitrophenyl)methylene)-2,6,4,6- Tetraacetate -,N-(Phenylmethylene)-2,3,4,6-Tetraacetate & CHEMICAL ABSTRACTS, Band 102, Nr. 7, 18. Februar 1985, (Columbus, Ohio US), G. WESTPHAL et al.: "Studies on the Maillard Reaction. Part 12. Formation of a Bisgluco-Sylamine Derivative", siehe seite 487, Zusammenfassung Nr. 60884, & Nahrung 1984, vol. 82, no.8, pages 809-814 * |
| CHEMICAL ABSTRACTS, Ninth Colletctive Index, Bande 76-85, 1972-1976, Formulas, (Columbus, Ohio, US), siehe seite 11528, C21H24N2011 beta-D-Glucopyranosylamine, N-((3-Nitrophenyl)- Methylene)-2,3,4,6-Tetraacetate C21H24N2O12, beta-D-Glucopyranosylamine, N-((2-Hydroxy-5-Nitrophenyl)Methylene - 2,3,4,6-Tetraacetate und seite 11560, C21H25NO10, beta-D-Glucopyranosylamine, N-((2-Hydroxyphenyl) Methylene)-2,3,4,6-Tetraacetate -,N-((4-Hydroxyphenyl)Methylene)-2,3,4,6-Tetraacetate & Chemical Abstract, Band 83, Nr. 3, 21. Juli 1975, (Columbus, Ohio, US), S.H. DOSS et al.: "NMR Studies on the Effect of the Nitrogen Atom on the Anomeric Proton of beta-D-Glucopyranosides", siehe seiten 542-543, Zusammenfassung Nr. 28518n, & Rev. Roum. Chim. 1974, vol. 19, no. 11, pages 1767-1772 * |
| Chemische Berichte, Band 106, 1973, Verlag Chemie GmbH, (Weinheim, DE), K. WEINGES et al.: "Die Asymmetrische Strecker-Synthese von Aliphatischen alfa-Methyl-alfa-Aminosauren", seiten 2291-2297 siehe seite 2291, Zusammenfassung * |
| Journal of the Chemical Society, Chemical Communications, Nr. 1, 7. Januar 1976, G. MacKENZIE et al.: "Synthesis of Analogues of 5-Aminoimidazole Ribonucleotides and Their Effects as Inhibitors and Substrates of the Enzymes, Phosphoribosylaminoimidazole Carboxylase and Phosphoribosylaminoimidazole-Succinocarboxamide Synthetase Involved in the Biosynthesis of Purine Nucleotides de Novo", seiten 453-455 siehe seite 454, Verbindung Ib * |
| The Journal of Organic Chemistry, Band 43, Nr. 10, 12. Mai 1978, American Chemical Society, (US). R.J.M. NOLTE et al.: "Poly(Iminomethylenes). 6. Synthesis and Polymerization of alfa- and beta-D-Glucopyranosyl Isocyanide" seiten 1972-1975 siehe seite 1972, Schema 1, Verbindung 5a * |
| The Journal of Organic Chemistry, Band 49, Nr. 10, 18. Mai 1984, American Chemical Society, (US), S.-Y. CHEN et al.: "Total Synthesis of Two Furanomycin Steroisomers" seiten 1769-1772 siehe seite 1770, spalte 1, zeilen 85-35 * |
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1994015941A1 (fr) * | 1993-01-14 | 1994-07-21 | Akzo N.V. | α-AMINONITRILES DERIVES D'UN SUCRE AMINE |
| FR2721612A1 (fr) * | 1994-06-23 | 1995-12-29 | Idm | Nouveaux dérivés d'oligosides, leur procédé de préparation et leurs applications. |
| WO1996000229A1 (fr) * | 1994-06-23 | 1996-01-04 | I.D.M. Immuno-Designed Molecules | Nouveaux derives d'oligosides, leur procede de preparation et leurs applications |
| US6251858B1 (en) | 1994-06-23 | 2001-06-26 | I.D.M. Immuno-Designed Molecules | Derivatives of oligosides, their process of preparation and their applications |
| WO2003006474A3 (fr) * | 2001-07-11 | 2003-05-01 | Schering Ag | Procede de production de 1-o-glycosides peracyles |
| US6831164B2 (en) | 2001-07-11 | 2004-12-14 | Schering Aktiengesellschaft | Process for the production of peracylated 1-0-glycosides |
| CN1300090C (zh) * | 2005-03-02 | 2007-02-14 | 杭州师范学院 | 一种芳基乙酸的制备方法 |
| US9036890B2 (en) | 2012-06-05 | 2015-05-19 | Outerwall Inc. | Optical coin discrimination systems and methods for use with consumer-operated kiosks and the like |
| US9594982B2 (en) | 2012-06-05 | 2017-03-14 | Coinstar, Llc | Optical coin discrimination systems and methods for use with consumer-operated kiosks and the like |
| US8967361B2 (en) | 2013-02-27 | 2015-03-03 | Outerwall Inc. | Coin counting and sorting machines |
| US9022841B2 (en) | 2013-05-08 | 2015-05-05 | Outerwall Inc. | Coin counting and/or sorting machines and associated systems and methods |
| US9443367B2 (en) | 2014-01-17 | 2016-09-13 | Outerwall Inc. | Digital image coin discrimination for use with consumer-operated kiosks and the like |
Also Published As
| Publication number | Publication date |
|---|---|
| DE3624376A1 (de) | 1988-01-28 |
| EP0274515A1 (fr) | 1988-07-20 |
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