SYNTHESIS OF N-ACETYLSUGAR-BETA-TRANS-GLYCOSIDES - FACILE ONE-POT TRANSGLYCOSYLATION OF EPOXYPENTYL TRI-O-ACETYL-N-ACETYLGLUCOSAMINE

被引：14

作者：

BOLDT, PC ^{[1
]}

SCHUMACHERWANDERSLEB, MHMG ^{[1
]}

PETER, MG ^{[1
]}

机构：

[1] UNIV BONN,INST ORGAN CHEM & BIOCHEM,GERHARD DOMAGK STR 1,W-5300 BONN 1,GERMANY

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 11期

关键词：

D O I：

10.1016/0040-4039(91)80344-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Glycosides 10 and 11 were prepared from epoxypentyl B-D-N-ace-tylglucosamine 8 under mild conditions, using TMS triflate as the promotor. Presumably, this novel reaction proceeds via in situ activation of the intermediate oxazoline 9.

引用

页码：1413 / 1416

页数：4

共 16 条

[1] DIRECT ELABORATION OF PENT-4-ENYL GLYCOSIDES INTO DISACCHARIDES
FRASERREID, B
KONRADSSON, P
MOOTOO, DR
UDODONG, U
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (12) : 823 - 825
[2] FERRIC CHLORIDE-CATALYZED GLYCOSYLATION OF ALCOHOLS BY 2-ACYLAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSE 1-ACETATES
KISO, M
ANDERSON, L
[J]. CARBOHYDRATE RESEARCH, 1979, 72 (JUL) : C12 - C14
[3] PROTECTED GLYCOSIDES AND DISACCHARIDES OF 2-AMINO-2-DEOXY-D-GLUCOPYRANOSE BY FERRIC CHLORIDE-CATALYZED COUPLING
KISO, M
ANDERSON, L
[J]. CARBOHYDRATE RESEARCH, 1985, 136 (FEB) : 309 - 323
[4] SYNTHESIS OF GLYCOPEPTIDES, PARTIAL STRUCTURES OF BIOLOGICAL RECOGNITION COMPONENTS
KUNZ, H
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1987, 26 (04): : 294 - 308
[5] KUNZ H, 1987, ANGEW CHEM, V99, P297
[6] EPOXYALKYL OLIGO-(-]4)-BETA-D-GLUCOSIDES AS ACTIVE-SITE-DIRECTED INHIBITORS OF CELLULASES
LEGLER, G
BAUSE, E
[J]. CARBOHYDRATE RESEARCH, 1973, 28 (01) : 45 - 52
[7] STANNOUS TRIFLATE MEDIATED GLYCOSIDATIONS - A STEREOSELECTIVE SYNTHESIS OF 2-AMINO 2-DEOXY-BETA-D-GLUCOPYRANOSIDES DIRECTLY WITH THE NATURAL N-ACETYL PROTECTING GROUP
LUBINEAU, A
GALLIC, JL
MALLERON, A
[J]. TETRAHEDRON LETTERS, 1987, 28 (42) : 5041 - 5044
[8] NORMAL-PENTENYL 2-AMINO-2-DEOXY GLYCOSIDES UNDERGO STEREOSELECTIVE COUPLING UNDER MILD, CHEMOSPECIFIC CONDITIONS
MOOTOO, DR
FRASERREID, B
[J]. TETRAHEDRON LETTERS, 1989, 30 (18) : 2363 - 2366
[9] TRIMETHYLSILYL TRIFLUOROMETHANESULFONATE AS AN EFFECTIVE CATALYST FOR GLYCOSIDE SYNTHESIS
OGAWA, T
BEPPU, K
NAKABAYASHI, S
[J]. CARBOHYDRATE RESEARCH, 1981, 93 (01) : C6 - C9
[10] ADVANCES IN SELECTIVE CHEMICAL SYNTHESES OF COMPLEX OLIGOSACCHARIDES
PAULSEN, H
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1982, 21 (03): : 155 - 173

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