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

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

Green Chem., 2014, Advance Article
DOI: 10.1039/C4GC00770K, Communication

Yuchao Lu,^a   Peng Wei,^a   Yuxin Pei,*^a   Hengfu Xu,^a  Xiaoting Xin^a and   Zhichao Pei*^ab  

 

*Corresponding authors

^aState Key Laboratory of Crop Stress Biology for Arid Areas and College of Science, Northwest A&F University, Yangling, People’s Republic of China 
E-mail: peizc@nwafu.edu.cn, peiyx@nwafu.edu.cn;
Fax: +86 2987092769 ;
Tel: +86 2987091196

^bAttana AB, Stockholm, Sweden

A novel method for an efficient regioselective acetylation of carbohydrates and diols in aqueous solution is described.

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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