A novel convergent strategy for the construction of oligosaccharides using TIPS-protected glycosides. Synthesis of fragments related to glycolipids of Mycobacterium smegmatis

Article abstract of DOI:10.1016/S0040-4039(00)60999-1

4,6-O-Pyruvylated glucosides 1 were converted to the corresponding glucosyl fluorides 3 and 2,3-O-TIPS-protected glucopyranosides 5, respectively. Lewis-acid-catalyzed coupling of 3 and 5 afforded the pyruvylated disaccharides 6 one of which was further converted via the dissacharide donor 8 to di- and trisaccharide fragments of Mycobacterium smegmatis.