Synthesis of 2,3,6-Trideoxysugar-Containing Disaccharides by Cyclization and Glycosidation Through the Sequential Activation of Sulfoxide and Methylsulfanyl Groups in a One-Pot Procedure.

✍ Scribed by Toru Amaya; Daisuke Takahashi; Hiroshi Tanaka; Takashi Takahashi

• Publisher: John Wiley and Sons
• Year: 2003
• Weight: 192 KB
• Volume: 34
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.200333194

✦ Synopsis

Synthesis of 2,3,6-Trideoxysugar-Containing Disaccharides by Cyclization and Glycosidation Through the Sequential Activation of Sulfoxide and Methylsulfanyl

Groups in a One-Pot Procedure. -A novel method for the synthesis of 2,3,6-trideoxyglycosides by one-pot sequential cyclization and subsequent glycosidation is reported. The reaction occurs with predominant formation of the α-glycosides at low temperatures. A number of functional groups like phenylsulfanyl, glycosylic fluoride, Bz, Mbz and Bn is tolerated and the desired disaccharides are obtained in good to excellent yields. -(