Mild and practical synthesis of 5-thio-D-glucopyranose and its pentaacetate derivatives

被引：0

作者：

Yanjun, Chen ^{[1
,2
]}

Rui, Zhang ^{[2
]}

Haiqian, Dong ^{[2
]}

机构：

[1] Ningbo Polytech, Ningbo Key Lab High Performance Petr Resin Prepara, Ningbo 315800, Peoples R China

[2] Ningbo Polytech, Coll Chem Engn, Ningbo 315800, Peoples R China

来源：

TETRAHEDRON | 2024年 / 163卷

关键词：

Synthesis; D; -glucofuranose; 6-Episulphide; Mild conditions;

D O I：

10.1016/j.tet.2024.134164

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Two synthetic approaches for 5-thio-D-glucopyranose (5-TDGP) and its pentaacetates were described, focusing on different protective groups such as tert-butyldimethylsilyl and benzoyl employed to protect 3-OH. These protective groups were easily introduced from the beginning and can be removed during transformation from the corresponding mesylate of alpha-D-glucofuranose to 5,6-episulfide under mild conditions. In addition, a few purification manipulations were required for each approach. More importantly, 5-TDGP can be prepared using the two approaches starting from 200 g of starting material in 66.08 % and 64.4 % overall yields, respectively.

引用

页数：5

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