An approach for disaccharide chiron synthesis using a Ferrier-type rearrangement

作者：Komor Katarzyna^*; Szeja Wieslaw; Bieg Tadeusz; Kuznik Nikodem; Pastuch Gawolek Gabriela; Komor Roman

来源：Tetrahedron Letters, 2014, 55(27): 3709-3712.

DOI：10.1016/j.tetlet.2014.05.025

• Chiral synthons
• Glycosylation
• Glycals
• Ferrier-type rearrangement
• Phase-transfer conditions

We report a new approach for the synthesis of new chiral synthons in which two unsaturated sugars are linked via a glycosidic bond. The di-unsaturated disaccharide can be further functionalized using effective, highly selective methods and used in convergent syntheses of relatively complex glycoconjugates. Our approach utilizes in situ generation of active glycosyl donors via Ferrier-type rearrangement under phase-transfer conditions and subsequent reaction with a nucleophile.

• 出版日期2014-7-2