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(2S,3S)-1,2-环氧基-3-叔丁氧酰胺基-4-苯丁烷的合成 被引量：1

Synthesis of(2S,3S)-1,2-epoxy-3-(Boc-amino)-4-phenylbutane
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摘要 以(S)-苯丙氨酸为原料,经氨基保护、与对硝基苯酚成酯后与硫叶立德反应制得(S)-1-氯-3-叔丁氧酰胺基-4-苯基-2-丁酮(3);3经Meerwein-Poondrf-Verley还原、环合等反应合成了HIV-1蛋白酶抑制剂的关键中单体——(2S,3S)-1,2-环氧基-3-叔丁氧酰胺基-4-苯丁烷,总收率约45%,其结构经1H NMR和MS确证。 A key intermediate for preparing HIV-1 protease inhibitors, （2S, 3S） -1,2-epoxy-3- （ Boc- amino）-4-phenylbutane in overall yield of about 45%, was synthesized from （S）-phenylalanine by protection, esterification with 4-nitrophenol, the reaction of the ester with dimethyl sulfoxonium methylide, subsequent Meerwein -Poondrf- Verley reduction and cyclization. The structure was confirmed by 1H NMR and MS.
作者 谌志华 徐辉 庄璐 盖涛 马红梅 虞心红
机构地区 上海奥奇医药科技有限公司 华东理工大学药学院上海市新药设计重点实验室
出处 《合成化学》 CAS CSCD 北大核心 2013年第3期361-363,共3页 Chinese Journal of Synthetic Chemistry
基金 国家自然科学基金资助项目(NSFC-20972051) 上海市科委科技支撑项目(12431900900 12431900902) 上海市新药设计重点实验室资助项目(11DZ2260600)
关键词 HIV-1蛋白酶抑制剂 (2S 3S)-1 2-环氧基-3-叔丁氧酰胺基-4-苯丁烷 中间体 药物合成 HIV-1 protease inhibitor intermediate drug synthesis
分类号 O625.63 [理学—有机化学] R914.5 [医药卫生—药物化学]
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参考文献9

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共引文献1

同被引文献11

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合成化学
2013年 第3期

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