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Synlett 1998; 1998(3): 304-306
DOI: 10.1055/s-1998-1629
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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
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Publication History

Publication Date:
31 December 2000 (online)

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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