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

页码：7783 / 7786

页数：4

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