Synthesis of a novel class of sulfonium ions as potential inhibitors of UDP-galactopyranose mutase

被引：24

作者：

Ghavami, A ^{[1
]}

Chen, JJW ^{[1
]}

Pinto, BM ^{[1
]}

机构：

[1] Simon Fraser Univ, Dept Chem, Burnaby, BC V5A 1S6, Canada

来源：

CARBOHYDRATE RESEARCH | 2004年 / 339卷 / 02期

基金：

加拿大自然科学与工程研究理事会;

关键词：

galactofuranose; UDP-galactopyranose mutase inhibitors; salacinol analogues; sulfonium salt;

D O I：

10.1016/j.carres.2003.09.036

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Two sulfonium salts of 1,4-anhydro-4-thio-D-galactitol, with structures related to the known sulfonium salt glycosidase inhibitor, salacinol, have been synthesized as potential inhibitors of UDP-galactopyranose mutase. The synthetic strategy relies on the alkylation reaction of 1,4-anhydro-2,3,5,6-tetra-O-benzyl-4-thin-D-galactitol at the sulfur atom with 2,4-O-benzylidene-D- or -L-erythritol-1,3-cyclic sulfate. In each case, the reaction proceeded stereoselectively to yield only one stereoisomer at the stereogenic sulfur atom. The effect of the polar solvent, 1,1,1,3,3,3-hexafluoroisopropanol (HFIP), in promoting high-yielding reactions is highlighted. The target compounds are then obtained by hydrogenolysis. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：401 / 407

页数：7

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