THE INSITU ACTIVATION OF THIOGLYCOSIDES WITH BROMINE - AN IMPROVED GLYCOSYLATION METHOD
THE INSITU ACTIVATION OF THIOGLYCOSIDES WITH BROMINE - AN IMPROVED GLYCOSYLATION METHOD
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DOI：
10.1021/jo00296a055
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发表时间：
1990-04-27
影响因子：
3.6
通讯作者：
BUNDLE, DR
中科院分区：
文献类型：
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作者：
KIHLBERG, JO;LEIGH, DA;BUNDLE, DR
通过在糖基受体和促进剂（如三氟甲磺酸银或氰化汞）存在下用溴处理，原位完成硫代糖苷向1，2-反式-或1，2-顺式-O-糖苷的一步转化。这种温和的“一锅法”程序以优异的产率得到O-糖苷，具有高立体化学控制，即使是不反应的和落后的糖基受体。反应条件与各种保护基团如乙酸酯、苯甲酸酯、苄基酯、N-邻苯二甲酰亚氨基和亚苄基缩醛相容。
A one-step conversion of thioglycosides into 1,2-trans- or 1,2-cis-O-glycosides was accomplished, in situ, by treatment with bromine in the presence of a glycosyl acceptor and a promoter such as silver triflate or mercuric cyanide. This mild "one-pot" procedure gives O-glycosides in excellent yields with high stereochemical control, even with unreactive and hindred glycosyl acceptors. The reaction conditions are compatible with various protection groups such as acetates, benzoates, benzyl esters, N-phthalimido groups, and benzylidene acetals.