Download PDF
Synlett 1998; 1998(3): 304-306
DOI: 10.1055/s-1998-1629
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.

Synthesis of 4-Hydroxy-2,6-bis(hydroxymethyl)tetrahydropyran-2-carbaldehyde Derivatives

Debra Turner* , Pierre Vogel
  • *Section de Chimie de l'Université, BCH-Dorigny, 1015 Lausanne, Switzerland
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

Cycloaddition of 1,3-dibromo-2-oxyallyl cation to 2-(benzyloxymethyl)furan provided a 8-oxabicyclo[3.2.1]hept-6-en-3-one derivative that was transformed into (2RS,3SR,4SR,5SR,6SR)-3,4-dibromo-2-benzyloxymethyl-2,6-bis(hydroxymethyl)-4-(methoxymethyloxy)tetrahydropyran. Selective protection and oxidation produced a protected 3,5-dibromo-4-hydroxy-2,6-bis(hydroxymethyl)tetrahydropyran-2-carbaldehyde that could be used to carry out cross-aldolisations, opening an approach to the synthesis of C-disaccharide analogues mimicking sialic acid glycosides.

[4 + 3]-cycloaddition - 8-oxabicyclo[3.2.1]hept-6-en-3-one - C-glycosides - sialic acid mimetics> - cross-aldolisations

      >