红景天活性成分络塞维的合成
投稿时间:2021-01-03  修订日期:2021-03-16  点此下载全文
引用本文:刘航,李安鹏,赵庆杰,徐伟.红景天活性成分络塞维的合成[J].药学实践杂志,2021,39(2):130~133
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作者单位E-mail
刘航 福建中医药大学药学院福建 福州 350100  
李安鹏 海军军医大学药学院上海 200433  
赵庆杰 海军军医大学药学院上海 200433  
徐伟 福建中医药大学药学院福建 福州 350100 2000017@fjtcm.edu.cn 
基金项目:科技部重大新药创制专项(2018ZX09J18108-001-002)
中文摘要:目的 研究红景天活性成分络塞维(rosavin)的化学全合成方法。方法 以β-D-五乙酰葡萄糖、1-羟基-2,3,4-三乙酰阿拉伯吡喃糖、肉桂醇为起始原料,经1-位选择性脱乙酰基、糖苷化反应、葡萄糖6-OH选择性保护及脱保护等8步反应制备目标化合物。结果 以高收率成功获得目标产物络塞维,结构经ESI-MS和1H-NMR、13C-NMR确证。首次报道以叔丁基二苯基氯硅烷高选择性、高收率保护6-OH的技术途径。结论 该合成路线具有操作简单,收率高,安全性好等优点。
中文关键词:红景天  络塞维  全合成  选择性保护
 
Synthesis of the active ingredient rosavin of Rhodiola rosea
Abstract:Objective To establish the chemical synthesis of the active ingredient rosavin of Rhodiola rosea.Methods β-D-pentaacetylglucose, 1-hydroxy-2,3,4-triacetylarabinose and cinnamyl alcohol were used as starting materials. The target compound was prepared by 1-position selective of β-D-pentaacetylglucose deacetylation, glycosylation reaction, glucose 6-OH selective protection and deprotection and other 8-step reactions.Results The target product, rosavage, was successfully obtained with high yield. The structure was confirmed by ESI-MS, 1H-NMR and 13C-NMR. The protection of 6-OH with high selectivity and high yield of tert-butyldiphenyl chlorosilane played a vital role in the synthesis process,.Conclusion The synthetic route has the advantages of simple operation, high yield, and good safety.
keywords:Rhodiola rosea  rosavin  total synthesis  selective protection
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