一步法合成9-去氧-8a-氮杂-8a-同型红霉素A  

Synthesis of 9-Deoxo-8a-aza-8a-homoerythromycin A by One-step

作　　者：王建华[1] 江志尧[1] 

机构地区：[1]重庆大学生物工程学院,重庆400044

出　　处：《合成化学》2010年第2期265-268,共4页Chinese Journal of Synthetic Chemistry

基　　金：国家科技支撑计划资助项目(2007BAD51B05);重庆市科技攻关计划资助项目(CSTC2009AB1043)

摘　　要：以（9Z）-9-去氧-9-羟基亚胺基红霉素A为原料，甲醇／水为反应体系，对甲苯磺酰氯为催化剂，硼氢化钠为还原剂，首次用一步法合成了9-去氧-8a-氮杂-8a-同型红霉素A，其结构经1^H NMR和FAB—MS表征。在pH8-9，于-3℃反应9h的较佳反应条件下，收率94．1％，纯度93．0％。One-step method was applied to the synthesis of 9-deoxo-8a-aza-8a-homoerythromycin A for the first time from （9Z）-9-deoxo-9-hydroxyiminoerythromycin A by Beckmann＇ s rearrangement using methanoL/water as the solvent, p-toluene sulfonyl chloride as the catalyst, and sodium boro- hydride as the reductant. The structure was characterized by 1^H NMR and FAB-MS. The yield was 94.1% with purity 93.0% by the reaction at - 3 ℃ for 9 h in solution of pH 8 - 9.

关 键 词：(9Z)-9-去氧-9-羟基亚胺基红霉素A 9-去氧-8a-氮杂-8a-同型红霉素A 贝克曼重排 一步法 药物合成 

分 类 号：R914.5[医药卫生—药物化学] O621.3[医药卫生—药学]