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 Xina 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.

http://pubs.rsc.org/en/Content/ArticleLanding/2014/GC/C4GC00770K?utm_source=feedburner&utm_medium=feed&utm_campaign=Feed%3A+rss%2FGC+%28RSC+-+Green+Chem.+latest+articles%29#!divAbstract

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