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Citation: LI Jun-Ting, LV Xia, TANG Yan-Hui, ZHANG Yun-Zhi, XUE Jia-Lu, WANG Zhao-Xia. Synthesis of o-Chloro-benzoquinonyl C-Glycopyranosides in High Regioselectivity[J]. Chinese Journal of Applied Chemistry, ;2009, 26(6): 651-656. shu

Synthesis of o-Chloro-benzoquinonyl C-Glycopyranosides in High Regioselectivity

1.
Laboratory for Advanced Material, Institute of Fine Chemicals, East China University of Science and Technology, Shanghai 200237

Corresponding author: WANG Zhao-Xia,
Received Date: 16 May 2008
Available Online: 23 June 2008
Fund Project: 国家自然科学基金(20576034) (20576034)上海市自然科学基金(05ZR14040)资助项目 (05ZR14040)

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·Et₂O,O-chloro-hydroquinonyl C-glycosides 5a and 5b can also be obtained through addition reaction and hydrolyzation involving benzoquinonyl C-glycosides and Me₃SiCl 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.
- chlorination,
- benzoquinone,
- hydroquinone,
- aryl C-glycoside
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