Regioselective acetylation of carbohydrates and diols catalyzed by tetramethyl-ammonium hydroxide in water

Literature Information

Publication Date 2014-07-31
DOI 10.1039/C4GC00770K
Impact Factor 10.182
Authors

Yuchao Lu, Peng Wei, Yuxin Pei, Hengfu Xu, Xiaoting Xin


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Abstract

A novel method for an efficient regioselective acetylation of carbohydrates and diols in aqueous solution is described. Treatment of substrates with 1-acetylimidazole, and tetramethyl-ammonium hydroxide (TMAH) in water under mild conditions gave highly regioselective acetylation for primary hydroxyl groups. This discovery provides an eco-friendly way for selective acetylation of non-protected glycosides and diols in water, avoiding the use of toxic organic solvents and the necessity of pre-protection of secondary hydroxyl groups.

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