Sugar acetates as glycosylating agents in oligosaccharide synthesis

✍ Scribed by V.A. Nesmeyanov; S.E. Zurabyan; A.Ya. Khorlin

• Publisher: Elsevier Science
• Year: 1973
• Tongue: French
• Weight: 209 KB
• Volume: 14
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)79815-7

✦ Synopsis

Fully acetylated sugars have been used as glycosylating agents in the synthesis of aryl glycosides in the presence of acidic catalysts or Lewis acids'. We now show that sugar acetates can also be used for this purpose in oligosaccharide synthesis. Treatment of 1,2,3,4-tetra-O-acetyl-6-0-trityl-~-D-glucopyranose (2) with ul.1~1 bromide and silver perchlorate gave rise to 2,3,4-tri-O-acetyl-1,6-anhydro+D-glucopyranose (11). In addition, analysis of the deacetylated reaction mixture showed the presence of glucose, gentiobiose, and oligosaccharides up to hexamer.