Synthesis of Glycosides with 4-(4-Hydroxyphenyl)-1,2,3-thia- and -selenadiazole Aglycones

被引：3
|
作者：
Pevzner, L. M. [1 ]
Petrov, M. L. [1 ]
Erkhitueva, E. B. [2 ]
Polukeev, V. A. [3 ]
Stepakov, A. V. [2 ]
机构：
[1] St Petersburg State Inst Technol Tech Univ, Moskovskii Pr 26, St Petersburg 190013, Russia
[2] St Petersburg State Univ, St Petersburg, Russia
[3] Inst Expt Med, St Petersburg, Russia
来源：
RUSSIAN JOURNAL OF GENERAL CHEMISTRY | 2019年 / 89卷 / 07期
关键词：
glycosylation; Konnigs-Knorr reaction; interphase catalysis; 1; 2; 3-thiadiazoles; semicarbazides; 3-selenadiazoles; BETA-D-GLUCOPYRANOSIDES;
D O I：
10.1134/S1070363219070089
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Glycosylation of 4-(4-hydroxyphenyl)-1,2,3-thia(selena)diazoles with 1-alpha-bromo-2,3,4,6-tetra-O-acetyl-D-glucopyranose, 1-alpha-bromo-2,3,4,6-tetra-O-acetyl-D-galactopyranose, and 1-alpha-bromo-2,3,5-tri-O-acetyl-D-xylopyranose under the conditions of interphase catalysis has afforded the corresponding acetylated glycosides. An alternative pathway of selenadiasole glycosides synthesis from semicarbazones of 1-beta-O-(4-acetylphenyl)-2,3,4,6-tetra-O-acetyl-D-glucopyranose, -2,3,4,6-tetra-O-acetyl-D-galactopyranose, and -2,3,5-tri-O-acetyl-D-xylopyranose via oxidation with selenium dioxide has been elaborated.
引用
收藏
页码：1398 / 1405
页数：8
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