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Synlett 2000; 2000(5): 0627-0628
DOI: 10.1055/s-2000-6642
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A Novel and Efficient Method for the Oxidative Removal of O-Benzyl Protective Groups of Carbohydrates by Tetrabutylammonium Peroxydisulfate

Fen-Er Chen* , Zuo-Zhong Peng, Han Fu, Ge Meng, Yu Cheng, Yin-Xiang Lü
  • *Department of Chemistry, Fudan University, Shanghai 200433, People's Republic of China; Fax + 86(21)65 64 20 21; E-mail: rfchen@fudan.edu.cn
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Publication Date:
31 December 2000 (online)

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Various benzyl ethers of carbohydrates have been selectively oxidized to the corresponding benzoate esters 2a - j with tetrabutylammonium peroxydisulfate under neutral conditions followed by debenzoylation with sodium methoxide to afford the debenzylated carbohydrates 3a - j in good overall yields. Noteworthy is that highly chemoselective reactions were achieved with the co-existence of other functionalities.

tetrabutylammonium peroxydisulfate - benzyl ethers - carbohydrates - debenzylation - protective group

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