Synthesis of Azide-armed [alpha]-1-C-Alkyl-imino-d-xylitol Derivatives as Key Building Blocks for the Preparation of Iminosugar Click Conjugates

Azide-armed α-1-C-alkyl-imino-d-xylitol derivatives have been efficiently prepared by way of olefin cross-metathesis in eight to nine steps and in an overall yield of 19% to 26% from 2,3,4-tri-O-benzyl-d-xylopyranose. Optimization of cleavage conditions of N-NAP-protected tertiary amines using DDQ i...

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Bibliographic Details
Published in:Journal of carbohydrate chemistry 2011-09, Vol.30 (7-9), p.559
Main Authors: Decroocq, Camille, Laparra, Laura Mamani, Rodriguez-Lucena, David, Compain, Philippe
Format: Article
Language:English
Subjects:
Derivatives
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Summary:Azide-armed α-1-C-alkyl-imino-d-xylitol derivatives have been efficiently prepared by way of olefin cross-metathesis in eight to nine steps and in an overall yield of 19% to 26% from 2,3,4-tri-O-benzyl-d-xylopyranose. Optimization of cleavage conditions of N-NAP-protected tertiary amines using DDQ in CH2Cl2-H2O (18:1) is also reported. The iminosugars synthesized will be used as key building blocks in the synthesis of multivalent iminosugars of biological interest by way of Cu(I)-catalyzed azide-alkyne cycloaddition reaction.
ISSN:0732-8303
1532-2327
DOI:10.1080/07328303.2011.610544