The synthesis of 2-azido C-glycosyl sugars

✍ Scribed by Carolyn R. Bertozzi; Mark D. Bednarski

• Book ID: 104216213
• Publisher: Elsevier Science
• Year: 1992
• Tongue: French
• Weight: 295 KB
• Volume: 33
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)79826-1

✦ Synopsis

&mmaty: 2-Azido C-glycosyl sugars can be prepared by the Lewis acid catalyzed addition of alkyl silanes to the nitrate glycosides of 2-azido sugars. The products are ozoniti to the coPresponding aldehyddes for further elaboration Amino sugars are integral components of glycoproteins, a class of natural products with crucial roles in biological recognition phenomena. * For example, 2=acetamido a-galactosides linked to serine or threonine are commonly found in O-linked glycopeptides such as the blood group and tumor associated antigens.2,3 C-glycosyl derivatives of these sugars can serve as stable analogs for biological recognition studies or as biologically active agents4 Efficient methods for the construction of 2-amino C-glycosyl compounds are therefore necessary for the generation of more complex carbohydrate analogs such as glycopeptides.