title: Regioselective azidotrimethylsilylation of carbohydrates and applications thereof.
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 carbohydrate substrates. Applications of the methodology for the synthesis of amino sugars, triazoles and azasugars are reported.
authors.affiliation: NPC(Microbes), CSIR-Indian Institute of Integrative Medicine, Canal Road, Jammu Tawi, India 180001.
authors.forename: Mallikharjuna Rao
authors.initials: MR
authors.lastname: L
authors.forename: Syed Khalid
authors.initials: SK
authors.lastname: Yousuf
authors.forename: Debaraj
authors.initials: D
authors.lastname: Mukherjee
authors.forename: Subhash Chandra
authors.initials: SC
authors.lastname: Taneja
mesh_terms: D001386:Azides / Q000737:chemistry*; D004187:Disaccharides / Q000737:chemistry*; D009005:Monosaccharides / Q000737:chemistry*; D012821:Silanes / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D001386:Azides; D004187:Disaccharides; D009005:Monosaccharides; D012821:Silanes; C438544:azidotrimethylsilane