Download PDF
Synlett 1996; 1996(6): 499-501
DOI: 10.1055/s-1996-5491
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

Per-O-Trimethylsilyl-α-L-Fucopyranosyl Iodide: A Novel Glycosylating Agent for Terminal α-L-Fucosylation

Taketo Uchiyama, Ole Hindsgaul*
  • *Department of Chemistry, University of Alberta, Edmonton, Alberta T6G 2G2 CANADA, Fax 403-492-7705; Email Ole.Hindsgaul@Ualberta.Ca
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

Trimethylsilylation of L-Fucose, followed by reaction with TMS-I, yields in situ the per-O-trimethylsilyl-α-L-fucopyranosyl iodide (2) without chromatography. Compound 2, in the absence of a promoter, reacts with alcohols to give α-L-fucopyranosides in good yields (45-90%). The net result is that hydrogenation is not an essential final step in the synthesis of fucosides and that benzyl groups may be used as temporary protecting groups in oligosaccharide synthesis involving terminal fucosylation.

Oligosaccharide synthesis - α-fucosylation

      >