Direct Synthesis of Glycosyl Chlorides from Thioglycosides

被引：0
|
作者：
Hoard, Daniel J. [1 ]
Sutar, Yogesh [1 ]
Demchenko, Alexei V. [1 ]
机构：
[1] St Louis Univ, Dept Chem, St Louis, MO 63103 USA
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 89卷 / 10期
关键词：
VERSATILE BUILDING-BLOCKS; N-ACETYLNEURAMINIC ACID; TRIFLUOROMETHANESULFONIC ACID; SULFURYL CHLORIDE; O-GLYCOSYLATION; DONORS; TRISACCHARIDE; GLYCOSIDATION; DERIVATIVES; EFFICIENT;
D O I：
10.1021/acs.joc.4c00244
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Reported herein is a new method for the direct synthesis of glycosyl chlorides from thioglycosides using sulfuryl chloride at rt. A variety of thioglycosides and thioimidates could be used as substrates. Both acid- and base-sensitive protecting groups were found compatible with these reaction conditions. Preliminary investigation of the reaction mechanism indicates chlorination of the leaving group at the anomeric sulfur as the key step of the reaction.
引用
收藏
页码：6865 / 6876
页数：12
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