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Synlett 1992; 1992(9): 759-761
DOI: 10.1055/s-1992-21485
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Improved Synthesis of β-Mannopyranosides by Intramolecular Aglycon Delivery

Frank Barresi* , Ole Hindsgaul
  • *Department of Chemistry, University of Alberta, Edmonton, Alberta T6G 2G2, Canada
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Publication Date:
08 March 2002 (online)

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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.

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