(S)-Camphorsulfonic acid catalyzed highly stereoselective synthesis of pseudoglycosides

被引：38

作者：

Gorityala, Bala Kishan ^{[1
]}

Cai, Shuting ^{[1
]}

Ma, Jimei ^{[1
]}

Liu, Xue-Wei ^{[1
]}

机构：

[1] Nanyang Technol Univ, Sch Phys & Math Sci, Div Chem & Biol Chem, Singapore 637371, Singapore

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2009年 / 19卷 / 11期

关键词：

Glycosylation; Ferrier rearrangement; alpha-Selectivity; 2,3-Unsaturated glycosides; 2,3-UNSATURATED GLYCOPYRANOSIDES; FERRIER REARRANGEMENT; NATURAL-PRODUCTS; FACILE SYNTHESIS; C-GLYCOSYLATION; EFFICIENT; GLYCALS; GLYCOSIDATION; DERIVATIVES; TRICHLORIDE;

D O I：

10.1016/j.bmcl.2009.04.003

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A mild and efficient synthesis of pseudoglycosides has been developed using metal free (S)-camphorsulfonic acid. (S)-CSA acts as an excellent catalyst for conversion of 2,4,6-tri-O-acetyl-D-glucal to 2,3-unsaturated O-glycosides. A wide range of biologically active natural products, alcohols and thiols could be coupled with glucal to give the desired pseudoglycosides in good to excellent yields with exclusive alpha-stereoselectivity. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：3093 / 3095

页数：3

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