红景天活性成分络塞维的合成

Synthesis of the active ingredient rosavin of Rhodiola rosea

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。

Objective To establish the chemical synthesis of the active ingredient rosavin of Rhodiola rosea.Methodsβ-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 ofβ-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,1 H-NMR and 13 C-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.