Glycosyl phenyl sulfoxides as a source of glycosyl carbanions:: Stereoselective synthesis of C-fucosides

被引：17
|
作者：
Jaramillo, C [1 ]
Corrales, G [1 ]
Fernández-Mayoralas, A [1 ]
机构：
[1] CSIC, Inst Quim Organ, Dept Quim Organ Biol, E-28006 Madrid, Spain
来源：
TETRAHEDRON LETTERS | 1998年 / 39卷 / 42期
关键词：
carbanions; carbohydrates; C-glycosides; addition reactions;
D O I：
10.1016/S0040-4039(98)01701-8
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Phenylsulfinyl-lithium exchange on glycosyl phenyl sulfoxides leads to configurationally stable anomeric carbanions which can react stereoselectively with electrophiles. Thus, the reaction of 3,4-O-isopropylidene-alpha-L-fucopyranosyl phenyl sulfoxide with tBuLi followed by treatment with isobutyraldehyde led to the alpha-configured C-glycoside; the beta-anomer furnished the corresponding beta-C-glycoside. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：7783 / 7786
页数：4
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