4.5 Article

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

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2009, Issue 23, Pages 3849-3852

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.200900424

Keywords

Glycosylation; Glycolipids; Sphingolipids; Tin; Ethers

Funding

  1. Direccion General de Educacion superior e Investigacion Cientifica (DGESIC) (Ministerio de Educacion y Ciencia, Spain) [CTQ-2008-01569/BQU]
  2. DURSI (Generalitat de Catalunya)
  3. Fons Social Euorpeu

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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)

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