Regioselective azidotrimethylsilylation of carbohydrates and applications thereof

SK Yousuf, D Mukherjee, SC Taneja

Index: Rao L., Mallikharjuna; Yousuf, Syed Khalid; Mukherjee, Debaraj; Taneja, Subhash Chandra Organic and Biomolecular Chemistry, 2012 , vol. 10, # 45 p. 9090 - 9098,9

Full Text: HTML

Citation Number: 2

Abstract

Azidotrimethylsilylation of carbohydrates (monosaccharides and disaccharides) has been achieved in high yields under Mitsunobu conditions. The azidation of carbohydrates is effected at 0° C essentially only at the primary alcoholic position in mono, di-and triols in protected/unprotected glycosides, whereas the remaining secondary hydroxyl groups got silylated. Surprisingly, no azidation of the secondary hydroxyls was observed in all the ...