| 程国强,王鹏,李明.4-苄氧羰基-木糖硫苷的合成[J].中国海洋药物,2022,41(1):57-62. |
| 4-苄氧羰基-木糖硫苷的合成 |
| Synthesis of 4-Benzyloxycarbonyl-Xylofuranosyl Thioglycoside |
| 投稿时间：2021-04-06 修订日期：2021-04-30 |
| DOI： |
| 中文关键词: 3′-表-Dragocin A 木糖硫苷 酶催化 Ho反应 |
| English Keywords:3-epi-Dragocin A xylofuranosyl thioglycoside enzyme catalysis Ho reaction |
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| 中文摘要: |
| 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。 |
| English Summary: |
| Objective In order to elucidate anticancer structure-activity relationship of dragoncin A, 4-benzyloxycarbohyl substituted xylofuranosyl building blocks should be prepared for synthesis of 3-epimer of dragoncin A. Methods Using 1,2:5,6-di-O-isopropylidene-glucofuranoside as starting material, 4-benzyloxycarbohyl xylofuranosyl thioglycoside was prepared relying on the Ho reaction, enzyme-catalyzed selective acetylation, protecting group manipulations, and functional group interconversion. Results Xylofuranosyl thioglycoside was accomplished in an overall 9% yield through an eight-step reaction sequence. This study sets a solid foundation for total synthesis of 3′-epi-Dragocin A. |
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