微波促进1,3-偶极环加成反应合成氮杂糖苷衍生物  

Efficient and Stereoselective Synthesis of Azasugar Derivatives Based on Microwave Assisted 1,3-Dipolar Cycloaddition

作　　者：李小六[1,2] 张宏波[1] 朱振刚[1] 陈华[1] 段科芳[1] 张平竹[1] 

机构地区：[1]河北大学化学与环境科学学院,河北省化学生物学实验室,保定071002 [2]北京大学天然药物及仿生药物国家重点实验室,北京100191

出　　处：《高等学校化学学报》2010年第9期1791-1797,共7页Chemical Journal of Chinese Universities

基　　金：国家自然科学基金(批准号:20672027;20972039);河北省自然科学基金(批准号:B2008000588);北京大学天然药物及仿生药物国家重点实验室开放课题基金(批准号:20080205)资助

摘　　要：利用微波促进氮杂糖硝酮(2)与丙烯酸类衍生物(3)发生1,3-偶极环加成反应,立体选择性地得到了一系列新的含异噁唑烷的氮杂糖衍生物(4),反应效率显著提高,反应时间由95h缩短为5～15min,收率由67%提高到78%～88%.利用NMR和HRMS等方法结合化合物(4d-1)的单晶结构确定了产物的结构和相对构型.In order to develop an efficient,practical and stereoselective method to access functionalized azasugar derivatives the microwave assisted 1,3-dipolar cycloaddition of azasugar nitrone and acrylates was investigated which afforded a series of novel azasugar derivatives containing an isoxazolindine moiety. The reaction was performed in a sealed microwave reactor at 110 ℃ in the solution of toluene and proceeded efficiently in yields up to 78% —88% within 5—15 min. The structures and configurations of the products were tentatively determined by 1H NMR,13C NMR,2D NMR and HRMS spectral analyses with comparison to the reported X-ray single crystallographic structure of the product 4d-1.

关 键 词：氮杂糖衍生物 微波促进有机合成 1 3-偶极环加成 立体选择性 

分 类 号：O629.13[理学—有机化学]