(3R,4R,5S)-4,5-环氧基-3-(1-乙基丙氧基)-1-环己烯1甲酸乙酯的合成

Synthesis of Ethyl(3R,4R,5S)-4,5-epoxy-3-(1-ethylpropoxy) -1-cyclohexene-1-carboxylate

目的 :(3R ,4R ,5S) 4,5 环氧基 3 (1 乙基丙氧基 ) 1 环己烯 1 甲酸乙酯是合成抗流感病毒新药奥塞米韦的关键中间体 ,本文对其不对称合成方法进行研究和改进。方法 :以 ( )莽草酸为起始物 ,经酯化、转酮化、还原开环、环氧化等 6步反应生成立体专一的目标产物。结果 :产物的化学结构经FT IR ,1 HNMR和1 3 CNMR得以确证。结论 :本方法较文献方法反应条件温和 。

AIM:Ethyl(3R,4R,5S)-4,5-epox y-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate is a key intermediate f or the preparation of novel anti-influenza drug oseltamivir and this study is to improve the chiral synthetic procedure of i t. METHOD:Title compound was stereoselectively prepared via a 6 -s tep reactions using(-)shikimic acid as starting material. RESULT: Its chemical structure was verified by FT-IR, 1 HNMR and 13 CNMR . CONCLUSION:Compared with the reported procedur e,this synthetic procedure is milder,an d has higher yield and lower cost.