高校化学工程学报Issue(5)：1167-1170,4.DOI:10.3969/j.issn.1003-9015.2015.05.021
N-（叔丁氧羰基）-2-氮杂双环[2.2.1]庚-5-烯-3-酮的手性拆分
Enantioselective Resolution of N-(tert-Butoxycarbonyl)- 2-azabicyclo[2.2.1]hept-5-en-3-one
李普瑞 1胡建建 1王晓川 1张玲玲 2王晓钟2
作者信息
- 1. 西安近代化学研究所，陕西西安 710065
- 2. 浙江大学化学工程与生物工程学院，浙江杭州 310027
- 折叠
摘要
Abstract
(−)-(1R,4S)-N-(tert-Butoxycarbonyl)-2-azabicyclo[2.2.1]hept-5-en-3-one is an important intermediate of abacavir which is widely used in AIDS treatment. This chemical was prepared with 2-azabicyclo-[2.2.1]hept-5-en-3-one(2) as the starting material in this study. The starting material(2) was first reacted with (Boc)2O to give the raceme (±)-N-(tert-Butoxycarbonyl)-2-azabicyclo[2.2.1]hept-5-en-3-one(3) via amidation. The key intermediate was preparedvia a prominent turnover from the raceme(3) with immobilized lipases, and its structure was identified by1H-NMR. The optimum conditions of the enzymatic reaction were as follows: Lipozyme RM IM andisopropyl elther were used as the enzyme reaction catalyst, and reaction solvent separatively, the mass ratio of enzyme: substrate 1.5/2.0 and the reaction temperature of 30℃. The yield can reach to 46.5% under these optimal conditions with enantiomeric excess up to 99%. This synthetic process is suitable for large-scale manufacture due to the cheap available material and higher catalytic activity and selectivity of the lipase.关键词
阿巴卡韦/N-(叔丁氧羰基)-2-氮杂双环2.2.1庚-5-烯-3-酮/固定化脂肪酶/手性拆分Key words
abacavir/N-(tert-Butoxycarbonyl)-2-azabicyclo[2.2.1]hept-5-en-3-one/immobilized lipases/chiral resolution分类
化学化工引用本文复制引用
李普瑞,胡建建,王晓川,张玲玲,王晓钟..N-（叔丁氧羰基）-2-氮杂双环[2.2.1]庚-5-烯-3-酮的手性拆分[J].高校化学工程学报,2015,(5):1167-1170,4.
