Efficient Synthesis of m-Chlorobenzoquinonyl C-Glycopyranosides

Chin. J. Org. Chem. ›› 2009, Vol. 29 ›› Issue (01): 78-81. Previous Articles Next Articles

Original Articles

高效合成氯代苯醌基碳糖苷

李军廷; 郑蓉蓉; 张云志; 吕遐; 唐燕辉*; 王朝霞*

(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)

收稿日期:2008-05-19 修回日期:2008-07-10 发布日期:2009-01-20
通讯作者: 唐燕辉*; 王朝霞*

Efficient Synthesis of m-Chlorobenzoquinonyl C-Glycopyranosides

Li, Junting; Zheng, Rongrong ; Zhang, Yunzhi ;Lü, Xia; Tang, Yanhui*; Wang, Zhaoxia*

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

Received:2008-05-19 Revised:2008-07-10 Published:2009-01-20
Contact: Tang, Yanhui*; Wang, Zhaoxia*

Abstract

A convenient and efficient synthesis of m-chlorobenzoquinonyl C-glycopyranosides 3a and 3b is reported. m-Chlorinated hydroquinonyl C-glycopyranosides 2a and 2b were synthesized by the addition of benzoquinone compounds 1a and 1b with CH3COCl/THF/H2O in high regioselectivities. Then the target compounds 3a and 3b were obtained after oxidation with ceric ammonium nitrate (CAN). The structures of the target compounds and intermediates were confirmed.

Key words: benzoquinone, chlorination, hydroquinone, aryl C-glycoside

Cite this article

Li, Junting; Zheng, Rongrong ; Zhang, Yunzhi ;Lü, Xia; Tang, Yanhui*; Wang, Zhaoxia*
. Efficient Synthesis of m-Chlorobenzoquinonyl C-Glycopyranosides[J]. Chin. J. Org. Chem., 2009, 29(01): 78-81.

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高效合成氯代苯醌基碳糖苷

Efficient Synthesis of m-Chlorobenzoquinonyl C-Glycopyranosides

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