Stereoselective synthesis of 2-deoxy-beta-C-aryl/alkyl glycosides using Prins cyclization: Application in the synthesis of C-disaccharides and differently protected C-aryl glycosides

摘要

2-Deoxy-beta-C-aryl/alkyl glycosides were synthesized from di-O-pivaloyl protected homoallylic alcohol derived from D-mannitol with various aldehydes via the Prins cyclization. The salient features of this methodology are high yields and excellent stereoselectivity. This method has also been successfully applied to the synthesis of differently protected 2-deoxy-beta-C-aryl glycosides and C-disaccharides. One of the 2-deoxy-beta-C-aryl glycosides was utilized as a glycosyl acceptor in the glycosylation to synthesize an O-linked disaccharides.