2,3-内醚-D-葡萄糖苷合成的探讨  

Study on Synthesis of 2,3-Anhydro-D-glucopyranoside

作　　者：佘戟[1] 

机构地区：[1]广东医学院化学教研室,广东湛江524023

出　　处：《化学世界》2005年第5期286-288,共3页Chemical World

摘　　要：对甲苯基4,6 苯亚甲基1 硫βD 葡萄糖苷(Ⅰ)经二步反应得到对甲苯基α2,3 内醚4,6 苯亚甲基1 硫βD 葡萄糖苷(Ⅲ)。在制备过程中,对2 OH和3 OH的对甲苯磺酰化反应活性差异进行了初步探讨。通过改变温度(-10～60°C)和改变Ⅰ和对甲基苯磺酰氯(TsCl)的物料比(1∶1～1∶3)的正交试验,仅分离得到对甲苯基3 对甲基苯磺酰基4,6 苯亚甲基1 硫βD 葡萄糖苷(Ⅱ),其产率不超过60%。同时,也对Ⅲ的分离纯化工艺进行了研究。p-Methylphenyl 2,3-anhydro-4,6-o-benzylidene-1-thio-β-D-allopyranoside (Ⅲ) has been prepared from p-methylphenyl 4,6-o-benzylidene-1-thio-β-D-glucopyranoside (Ⅰ). The difference in activity between 2-OH and 3-OH for the tosylation reaction has been explored. Orthogonal experiments in the temperature range of -10～60°C and in the Ⅰ and TsCl mass ratio range of 1∶1～1∶3 were conducted. Only p-methylphenyl 4,6-o-benzylidene-3-o-p-toluenesulfonyl-1-thio-β-D-glucopyranoside (Ⅱ) was isolated from the product, and its yield was no more than 60%. At the same time, the purification method of Ⅲ has been improved.

关 键 词：对甲苯磺酰化 葡萄糖苷 活性 环氧化合物 

分 类 号：TQ350.10[化学工程] O621[理学—有机化学]