Download PDF
Synlett 1992; 1992(9): 759-761
DOI: 10.1055/s-1992-21485
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.

Improved Synthesis of β-Mannopyranosides by Intramolecular Aglycon Delivery

Frank Barresi* , Ole Hindsgaul
  • *Department of Chemistry, University of Alberta, Edmonton, Alberta T6G 2G2, Canada
Further Information

Publication History

Publication Date:
08 March 2002 (online)

  PDF Download  Permissions and Reprints All articles of this category

The exclusive formation of the β-anomer derivatives of β-D-Manp-(1→4)-α-D-Glcp-OCH3 (9) and β-D-Manp-(1→4)-β-D-GlcNAcp-O(CH2)7CH3 (12) is shown to proceed in high yield using intramolecular aglycon delivery. The authentic α-anomers of 9 and 12 were chemically synthesized as reference standards and confirmed not to be formed in the reaction. This supports the complete stereoselective nature of this glycosylation reaction.