Download PDF
Synlett 1997; 1997(7): 851-853
DOI: 10.1055/s-1997-5756
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.

Use of Furanoid Glycals in Oligosaccharide Synthesis

Cornelis M. Timmers, Jeroen C. Verheijen, Gijsbert A. van der Marel, Jacobus H. van Boom*
  • *Leiden Institute of Chemistry, Gorlaeus Laboratories, University of Leiden, P.O. Box 9502, 2300 RA Leiden, The Netherlands, Fax: +71-5274307; E-mail: j.boom@chem.leidenuniv.nl
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

Furanoid glycals 3, 4 and 9, containing a 3-O-silyl protecting group, are readily epoxidized with DMD to give the respective shelf-stable α-1,2-anhydrofuranoses 7, 8 and 10. The latter oxiranes react smoothly and stereoselectively under the agency of ZnCl2 with a variety of primary and allylic secondary glycosyl acceptors (e.g. 1, 11-13) resulting in the exclusive formation of β-linked disaccharides (e.g. 14-18) in yields comparable to those obtained starting from 1,2-anhydropyranoses. Furthermore, the dimeric glucofuranoside 18 was transformed into the corresponding 2'-deoxyfuranoside 20, the β-mannofuranoside 21 and the (1→2)-branched furanoside 22.

glycal - furanoside - oligosaccharide - 1,2,-anhydrosugar - silyl protective group

      >