Synthesis of S-alpha- and -beta-D-glycosyl phosphorothioates and Se-alpha-D-glycosyl phosphoroselenoates from peracetylated monosaccharides

被引：5

作者：

Kudelska, W

机构：

[1] Laboratory of Organic Chemistry, Institute of Chemistry, Medical University, PL 90-151 Łódź

来源：

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS | 1996年 / 119卷

关键词：

glycosylation of phosphorothioates and phosphoroselenoates promoted by BF3 center dot Et2O; S-alpha-D-glycosyl and S-beta-D-glycosyl phosphorothioates Se-alpha-D-glycosyl phosphoroselinoates;

D O I：

10.1080/10426509608043472

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Ambident anions derived from phosphorothioates 5, 5a and phosphoroselenoates 6-7 were glycosylated by per-O-acetylated beta-D-hexopyranoses 1-2 in the presence of boron trifluoride etherate to yield S-alpha-o-glycosyl phosphorothioates 12-13 and Se-alpha-D-glycosyl phosphoroselenoates 14-16. The reaction of aliphatic phosphorothioates 3-4a with 1-2 leads to S-beta-D-glycosyl phosphorothioates 8-11 with high yield.

引用

页码：139 / 149

页数：11

共 12 条

[1]

BLUJ S, 1974, ROCZ CHEM, V48, P329

[2] THIONO-THIOLO REARRANGEMENT AND SOLVOLYSIS OF THE SECONDARY ALKYL PHOSPHOROTHIONATES .3. [J].