摘要
价廉易得的L-亮氨酸先以苄基同时保护氨基及羧基得(S)-2-(二苄胺基)-4-甲基戊酸苄酯,进而在碱性条件下与乙腈发生亲核取代反应得(S)-4-(二苄胺基)-6-甲基-3-氧代庚腈,再经硼氢化钠选择性还原羰基得(3S,4S)-4-(二苄胺基)-3-羟基-6-甲基庚腈,用双氧水氧化得(3S,4S)-4-(二苄胺基)-3-羟基-6-甲基庚酸,最后在Pd(OH)2/C-H2作用下脱掉苄基得到(3S,4S)-4-氨基-3-羟基-6-甲基庚酸,即(3S,4S)-statine。整个合成路线总产率为33.6%。
（3S,4S）-4-（Dibenzylamino）-3-hydroxy-6-methyl-heptanoic acid was synthesized from L-Leucine by protection of amino and carboxyl group to give（ S）-2-（ dibenzylamino）-4-methylbenzyl valerate,which was subjected to nucleophilic substitution with acetontrile and stereoselective reduction with NaBH4 to afford（3S,4S）-4-（dibenzylamino）-3-hydroxy-6-methylheptanenitrile,fol-lowed by oxidation with hydrogen peroxide to give（3S,4S）-4-（dibenzylamino）-3-hydroxy-6-methylheptanoic acid. Finally,depro-tection of benzyl group in presence of Pd（OH）2/C-H2 to achieve（3S,4S）-4-amino-3-hydroxy-6-methylheptanoic acid in an overall yield of about 33. 6%.
出处
《化学研究与应用》
CAS
CSCD
北大核心
2015年第5期675-678,共4页
Chemical Research and Application
基金
国家自然科学基金项目(21102055)资助
吉林省教育厅项目(2012339)资助
