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Synlett 1997; 1997(7): 851-853
DOI: 10.1055/s-1997-5756
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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
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Publication Date:
31 December 2000 (online)

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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