4-苄氧羰基-木糖硫苷的合成  

Synthesis of 4-benzyloxycarbonyl-xylofuranosyl thioglycoside

作　　者：程国强 王鹏[1] 李明[1,2] CHENG Guo-qiang;WANG Peng;LI Ming(Key Laboratory of Marine Drugs,Ministry of Education,School of Medicine and Pharmacy,Ocean University of China,Qingdao 266003,China;Laboratory for Marine Drugs and Bioproducts of Qingdao Pilot National Laboratory for Marine Science and Technology,Qingdao 266237,China)

机构地区：[1]中国海洋大学海洋药物教育部重点实验室,医药学院,山东青岛266003 [2]青岛海洋科学与技术试点国家实验室海洋药物与生物制品功能实验室,山东青岛266237

出　　处：《中国海洋药物》2022年第1期57-62,共6页Chinese Journal of Marine Drugs

基　　金：国家自然科学基金项目(21977088,21672194)资助。

摘　　要：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。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.

关 键 词：3′-表-dragocin A 木糖硫苷 酶催化 Ho反应 

分 类 号：R914[医药卫生—药物化学]