薯蓣皂苷元-葡萄糖C-苷类似物的合成  

Synthesis of Diosgenin-C-glucoside Analogue

作　　者：胡晓芳 马小锋[2] 赵晋忠[1] 张建刚[1] HU Xiao-fang;MA Xiao-feng;ZHAO Jin-zhong;ZHANG Jian-gang(Shanxi Agricultural University, Department of Basic Sciences, Shanxi 030801, China;Natural Products Research Centre, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041, China)

机构地区：[1]山西农业大学基础部,山西太谷030801 [2]中国科学院成都生物研究所天然产物研究中心,四川成都610041

出　　处：《合成化学》2021年第4期293-297,共5页Chinese Journal of Synthetic Chemistry

基　　金：山西省重点研发计划项目(201903D211006-1)。

摘　　要：采用汇集式合成策略,以葡萄糖为原料,经乙酰化、溴代、消除、硅炔基化、脱除保护基制得(2R,3R)-6-乙炔基-2-(羟甲基)-3,6-二氢-2H-吡喃-3-醇(5);以薯蓣皂苷元为原料,经磺酰化、叠氮化制得叠氮化薯蓣皂苷元(8);以5和8为原料,经Click反应合成薯蓣皂苷元-葡萄糖C-苷类似物(9),收率74%,其结构经^(1)H NMR,^(13)C NMR及HR-MS(ESI)表征。By using the convergent synthesis strategy,in one hand,started from glucose,after acetylation,bromination,elimination,silicoalkynyl,and global remove of the protecting groups,obtained(2R,3R)-6-acetylenyl-2-(hydroxymethyl)-3,6-dihydro-2H-pyrano-3-alcohols(5).In the other hand,diosgenin azide(8)was synthesized from diosgenin by sulfonylation and azidation.Diosgenin-C-glucoside analogue(9)was then obtained from compounds 5 and 8 via Click reaction.The structure was characterized by ^(1)H NMR,^(13)C NMR and HR-MS(ESI).

关 键 词：葡萄糖 薯蓣皂苷元 C-苷类似物 CLICK反应 合成 

分 类 号：O626[理学—有机化学]