Phase transfer catalysis toward the synthesis of O-, S-, Se- and C-glycosides

被引:38
作者
Carrière, D [1 ]
Meunier, SJ [1 ]
Tropper, FD [1 ]
Cao, S [1 ]
Roy, R [1 ]
机构
[1] Univ Ottawa, Dept Chem, Ottawa, ON K1N 6N5, Canada
基金
加拿大自然科学与工程研究理事会;
关键词
PTC; carbohydrate; substitution; thioglycoside; selenoglycoside; sialic acid;
D O I
10.1016/S1381-1169(99)00358-1
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Phase transfer catalysis (PTC) has been used for the synthesis of anomeric glycosyl derivatives, which included O-, S-, Se- and C- glycosides. These various glycosyl derivatives have been stereospecifically obtained from glycosyl halides 1, 2, 3, 14, 26. These reactions proceeded in generally good yields,;md were essentially complete within 3 h. (C) 2000 Elsevier Science B.V. All rights reserved.
引用
收藏
页码:9 / 22
页数:14
相关论文
共 43 条
[21]  
LEVY DE, 1995, CHEM C GLYCOSIDES, P13
[22]   NOVEL GLYCOSIDATION METHODOLOGY - THE USE OF PHENYL SELENOGLYCOSIDES AS GLYCOSYL DONORS AND ACCEPTORS IN OLIGOSACCHARIDE SYNTHESIS [J].
MEHTA, S ;
PINTO, BM .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (12) :3269-3276
[23]   PHASE-TRANSFER PROMOTED RUTHENIUM OXIDE OXIDATIONS OF CARBOHYDRATES .2. [J].
MORRIS, PE ;
KIELY, DE ;
VIGEE, GS ;
KOVAC, P .
JOURNAL OF CARBOHYDRATE CHEMISTRY, 1990, 9 (05) :661-673
[24]  
PARK WKC, 1995, CARBOHYDR LETT, V1, P179
[25]  
REINHARD B, 1994, LIEBIGS ANN CHEM, P193
[26]   PHASE-TRANSFER-CATALYZED SYNTHESIS OF N-ACETYLNEURAMINIC ACID ALPHA-THIOKETOSIDES AND INHIBITOR STUDIES WITH CLOSTRIDIUM-PERFRINGENS SIALIDASE [J].
ROTHERMEL, J ;
FAILLARD, H .
BIOLOGICAL CHEMISTRY HOPPE-SEYLER, 1989, 370 (10) :1077-1084
[27]   PHASE-TRANSFER-CATALYZED SYNTHESIS OF ARYL ALPHA-KETOSIDES OF N-ACETYLNEURAMINIC ACID - A 2-METHYLFLUORAN-6-YL GLYCOSIDE OF N-ACETYLNEURAMINIC ACID, 2-METHYL-6-(5-ACETAMIDO-3,5-DIDEOXY-ALPHA-D-GLYCERO-D-GALACTO-NONULOPYRANOSYLONIC ACID)XANTHENE-9-SPIRO-1'-ISOBENZOFURAN-3'-ONE, A NEW SUBSTRATE FOR NEURAMINIDASE ASSAY [J].
ROTHERMEL, J ;
FAILLARD, H .
CARBOHYDRATE RESEARCH, 1990, 196 :29-40
[28]  
ROTHERMEL J, 1992, LIEBIGS ANN CHEM, P799
[29]   PHASE-TRANSFER-CATALYZED SYNTHESIS OF A PHENYLSELENO ALPHA-KETOSIDE OF N-ACETYLNEURAMINIC ACID, (PHENYL 5-ACETAMIDO-3,5-DIDEOXY-D-GLYCERO-ALPHA-D-GALACTO-2-SELENONONULOPYRANOSID)-ONIC ACID - A NEW SIALIDASE INHIBITOR [J].
ROTHERMEL, J ;
FAILLARD, H .
CARBOHYDRATE RESEARCH, 1990, 208 :251-254
[30]   SYNTHESES OF GLYCOSYL PHOSPHATES BY PHASE-TRANSFER CATALYSIS [J].
ROY, R ;
TROPPER, FD ;
GRANDMAITRE, C .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1991, 69 (09) :1462-1467