Synthesis of fully and partially benzylated glycosyl azides via thioalkyl glycosides as precursors for the preparation of N-glycopeptides

✍ Scribed by János Kerékgyártó; Károly Ágoston; Gyula Batta; Johannis P. Kamerling; Johannes F.G. Vliegenthart

• Publisher: Elsevier Science
• Year: 1998
• Tongue: French
• Weight: 218 KB
• Volume: 39
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(98)01540-8

✦ Synopsis

Fully O-benzylated mono-, di-and trisaccharide glycosyl azides representing the reducing terminal of the core structure of N-glycans were synthesized. Totally and partially benzylated thioalkyl glucosamine glycosides were converted into the corresponding glycosyl azides with trimethylsilyl azide in the presence of methyl triflate. The 13-mannosidic linkage was created by C-2 epimerization of the initially introduced f3-D-glucounit via oxidation followed by stereoselective reduction with tetrabutylammonium borohydride.