Thiosugars, Part 3.: Preparation of methyl 2,3-di-O-mesyl-4,6-thioanhydro-α-D-galactopyranoside and methyl 2-O-mesyl-4,6-thioanhydro-α-D-gulopyranoside

被引：13

作者：

Adiwidjaja, G

Brunck, JS

Polchow, K

Voss, J

机构：

[1] Univ Hamburg, Inst Organ Chem, D-20146 Hamburg, Germany

[2] Univ Hamburg, Inst Mineral Petrog, D-20146 Hamburg, Germany

来源：

CARBOHYDRATE RESEARCH | 2000年 / 325卷 / 04期

关键词：

Mitsunobu reaction; thiosugars; 2-oxa-7-thiabicyclo[4.2.0]octanes; X-ray diffraction analysis; C-1(4)-alpha-D-gulopyranose derivative;

D O I：

10.1016/S0008-6215(00)00009-4

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 2-oxa-7-thiabicyclo[4.2.0]octane derivatives, 4 and 10, with the D-galacto and D-gulo configuration, respectively, were obtained from methyl alpha-D-glucopyranoside. The thietane cyclization involved a thio-Mitsunobu reaction resulting in a 6-thioacetate, which underwent selective base-catalyzed intramolecular nucleophilic substitution at a C-4 mesylate. The structures of 4 and 10 were elucidated by X-ray diffraction analysis. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：237 / 244

页数：8

共 30 条

[1] SIR92 - a program for automatic solution of crystal structures by direct methods [J].