基于D-木糖的新型手性氨基醇的合成  

Synthesis of New Chiral Amino Alcohol Based on D-xylose

作　　者：施梅[1] 周翔[1] 陈昌云[1] 

机构地区：[1]南京晓庄学院环境科学学院,江苏南京211171

出　　处：《南京晓庄学院学报》2016年第6期66-69,96,共5页Journal of Nanjing Xiaozhuang University

基　　金：江苏省高校自然科学研究项目(14KJD150006);江苏省大学生实践创新课题(201411460049X)

摘　　要：手性氨基醇作为催化剂广泛应用于多种不对称合成反应中.以天然D-木糖为原料,分别经异丙叉保护羟基,盐酸作用下选择性脱除保护基,羟基对甲苯磺酰化及亲核取代等4步反应,合成了两种新型手性氨基醇:1,2-O-异丙叉基-5-脱氧-5-吗啉基-α-D-木糖,产率38%;1,2-O-异丙叉基-5-脱氧-5-哌啶基-α-D-木糖,产率36%.对目标化合物及反应中间体的结构均进行1H NMR表征.Chiral amino alcohol is widely used in a variety of asymmetric reactions as catalysts. Two kinds of chiral amino alcohol, 1,2-O-isopropylidene-5-deoxy-5-morpholino-α-D-xylofuranoseand 1,2-O-isopropylidene-5-deoxy-5-piperidino-α-D-xylofuranose, were synthesized by a four-step reaction starting from natural D-xylose. Firstly, D-xy-lose was condensed with acetone under the catalyst of sulfuric acid and copper sulphate, and then underwent partial hydrolysis, p-tosylation of 5-hydroxyl group and nucleophilic substitution successively,with a total yield of 38% and 36% respectively. The target compounds and the key intermediates were characterized by 1 H NMR.

关 键 词：氨基醇 D-木糖 手性 合成 

分 类 号：O621.3[理学—有机化学]