4-苄氧羰基-木糖硫苷的合成

目的为研究海洋天然产物dragocin A抗肿瘤活性的构效关系,合成其C3′位差向异构体(3′-表-dragocin A)所需的木糖砌块。方法以1,2:5,6-二丙酮叉保护的呋喃葡萄糖为原料,通过Ho反应、酶催化选择性乙酰化和保护基操作及官能团转化,完成4-苄氧羰基-呋喃木糖硫苷的制备。结果通过8步反应,以9%的总收率制备了所需的木糖硫苷,为3′-表-dragocin A的全合成提供了物质基础。

Synthesis of 4-Benzyloxycarbonyl-Xylofuranosyl Thioglycoside

Objective To elucidate anticancer structure-activity relationship of dragocin A,4-benzyloxycarbohyl substituted xylofuranosyl building blocks need to be prepared for synthesis of 3-epimer of dragocin A.Methods Using 1,2:5,6-di-O-isopropylidene-glucofuranoside as starting material,4-benzyloxycarbohyl xylofuranosyl thioglycoside was prepared through the Ho reaction,enzyme-catalyzed selective acetylation,protection,deprotection,and functional group conversion.Results Xylofuranosyl thioglycoside was produced in an overall yield of 9%in eight steps.This study builds up a solid foundation for total synthesis of 3′-epidragocin A.