一条合成毛蕊花苷的新路线  

A New Approach to the Synthesis of Acteoside

作　　者：胡志飞 徐鹏[2] 俞飚 Hu Zhifei;Xu Peng;Yu Biao(School of Physical Science and Technology,ShanghaiTech University,Shanghai 201210;State Key Laboratory of Bioorganic and Natural Products Chemistry,Shanghai Institute of Organic Chemistry,Chinese Academy of Sciences,Shanghai 200032)

机构地区：[1]上海科技大学物质科学与技术学院,上海201210 [2]中国科学院上海有机化学研究所生命有机化学国家重点实验室,上海200032

出　　处：《有机化学》2020年第10期3439-3445,共7页Chinese Journal of Organic Chemistry

基　　金：国家重点研发计划(No.2018YFC0310900);国家自然科学基金(No.21621002);中国科学院前沿科学重点研究(No.ZDBS-LY-SLH030);中国科学院战略性先导科技专项(B类)(No.XDB20020000);王宽诚教育基金会资助项目。

摘　　要：毛蕊花苷(Acteoside)是苯丙素苷类天然产物中的代表性分子,具有广泛的生物活性.报道了一条新的合成毛蕊花苷的路线.在合成中,利用鼠李糖基邻炔基苯甲酸酯给体和2,3,4-三羟基葡萄糖硫苷在金(I)催化下的区域选择性糖苷化,得到关键的α-(1→3)连接二糖硫苷7-1,通过二糖的邻炔基苯甲酸酯给体合成苯丙素苷,进而完成了毛蕊花苷的合成.区域选择性的糖苷化减少了保护基操作步骤,缩短了合成路线.A new approach to the synthesis of acteoside,a prototypical phenylpropanoid glycoside with a variety of biological activities,has been developed.The synthesis employed a regioselective glycosylation as a key step,in which a gold(I)-catalyzed glycosylation of p-tolyl 6-O-acetyl-1-thio-β-D-glucopyranoside with peracetyl L-rhamnopyranosyl ortho-alkynylbenzoate led to the desiredα-(1→3)linked disaccharide 7-1 in a satisfactory yield.The resultant disaccharide was converted into the corresponding ortho-alkynylbenzoate donor and subjected to glycosylation with aglycone,subsequent deprotection of the protecting groups furnished acteoside.

关 键 词：毛蕊花苷 苯丙素苷 糖苷化 金(I)催化 

分 类 号：O629.13[理学—有机化学]