An Efficient Synthesis of Brominated C-Aryl Glycopyranoside

Chin. J. Org. Chem. ›› 2008, Vol. 28 ›› Issue (2): 321-324. Previous Articles Next Articles

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溴代芳香碳糖苷的高效合成方法

张云志，陈冠宇，陈国荣*

(华东理工大学精细化工研究所结构可控先进功能材料及其制备教育部重点实验室上海 200237)

收稿日期:2007-04-12 修回日期:2007-07-14 发布日期:2008-02-01
通讯作者: 陈国荣

An Efficient Synthesis of Brominated C-Aryl Glycopyranoside

ZHANG Yun-Zhi,CHEN Guan-Yu,CHEN Guo-Rong*

(Laboratory for Advanced Materials, Institute of Fine Chemical, East China University of Science and Technology,
Shanghai 200237)

Received:2007-04-12 Revised:2007-07-14 Published:2008-02-01
Contact: CHEN Guo-Rong

Abstract

Using SnCl₄ and CF₃CO₂Ag as catalysts, 2-(2,3,4,6-tetra-O-acetyl-β-D-glycopyranosyl)-1,4- dimethoxy-benzenes (4a and 4b) were prepared firstly, then using NH₄NO₃ as a catalyst under milder condition the bromination of 4a or 4b by N-bromosuccinimide (NBS) gave 2-(2,3,4,6-tetra-O-acetyl-β-D-gly-copyranosyl)-5-bromo-1,4-dimethoxy-benzene (1a or 1b) in high yields. The effect of the quantity of NBS and NH₄NO₃ on the bromination was discussed.

Key words: N-bromosuccinimide, C-aryl glycoside, ammonium nitrate, bromination

Cite this article

ZHANG Yun-Zhi,CHEN Guan-Yu,CHEN Guo-Rong*. An Efficient Synthesis of Brominated C-Aryl Glycopyranoside[J]. Chin. J. Org. Chem., 2008, 28(2): 321-324.

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溴代芳香碳糖苷的高效合成方法

An Efficient Synthesis of Brominated C-Aryl Glycopyranoside

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