Efficient Synthesis of β-Glycosphingolipids by Reaction of Stannylceramides with Glycosyl Iodides Promoted by TBAI/AW 300 Molecular Sieves

TBAI and acid-washed molecular sieves efficiently promoted the glycosylation of stannylceramides with glycosyl iodides. This direct glycosylation reaction reduces the overall number of synthetic steps and provides rapid access to beta-glycosphingolipids such as GalCer, beta-lactosylceramide, and iGB3 in good yield and with complete chemo- and stereoselectivity. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)