文献类型：期刊文献

中文题名：对氯醌基碳糖苷的高区域选择性合成方法

英文题名：Synthesis of o-Chloro-benzoquinonyl C-Glycopyranosides in High Regioselectivity

作者：李军廷 吕遐 唐燕辉 张云志 薛佳[马坴][1];王朝霞[1]

机构：[1]华东理工大学结构可控先进功能材料及其制备教育部重点实验室,精细化工研究所,上海200237

年份：2009

卷号：26

期号：6

起止页码：651

中文期刊名：应用化学

外文期刊名：Chinese Journal of Applied Chemistry

收录：CSTPCD;;北大核心:【北大核心2008】；CSCD:【CSCD2011_2012】；

基金：国家自然科学基金（20576034）和上海市自然科学基金（05ZR14040）资助项目

语种：中文

中文关键词：氯化;苯醌;氢醌;芳香碳糖苷

外文关键词：chlorination,benzoquinone,hydroquinone,aryl C-glycoside

摘要：报道2条反应条件温和、高效、实用的实验室合成对氯代醌基碳糖苷化合物的路线：其一路线是以芳香碳糖苷1a（1b）为起始原料,在硝酸铵催化下,与N-氯代丁二酰亚胺（NCS）反应获得对氯代芳香碳苷2a（2b）,经硝酸铈铵（CAN）脱甲基氧化,得到氯代醌基糖苷3a（3b）,总收率为88%（84%）;另一路线是通过三甲基氯硅烷在三氟化硼.乙醚作用下对苯醌碳苷4a（4b）的催化加成和水解反应,获得对氯代氢醌基碳苷5a（5b）,总收率为82%（76%）,而且5a（5b）与氯代醌基糖苷3a（3b）可以通过氧化与还原反应相互转化。
Two mild, efficient and practical methods to synthesize O-chloro-benzoquinonyl C-glycopyranosides are reported. One is that, using NH4NO3 as a catalyst, aryl C-glycosides 1a and 1b were chlorinated by N-chlorosuccinimide to afford O-chlorinated compounds 2a and 2b in high regioselectivity. The corresponding benzoquinonyl C-glycosides 3a and 3b were obtained after oxidization with cerium ammonium nitrate（CAN） in an overall yield of 88% and 84%, respectively. The other is that, under the catalysis of BF3 · Et2 O, O-chloro-hydroquinonyl C-glycosides 5a and 5b can also be obtained through addition reaction and hydrolyzation involving benzoquinonyl C-glycosides and Me3 SiCl in an overall yield of 82% and 76% , respectively. Additionally, corresponding hydroquinone and benzoquinone compounds can be transformed to each other through oxidation and reduction reactions.