Concise synthesis of C-1-cyano-iminosugars via a new Staudinger/aza Wittig/Strecker multicomponent reaction strategy

The Staudinger/aza Wittig/Strecker (SAWS) multicomponent reaction (MCR) sequence applied to azidodeoxy carbohydrate substrates leads smoothly in good yield and with excellent stereoselectivity to versatile C-glycosyl iminoalditol analogues which prove useful as building blocks en route to functional...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry letters 2014-06, Vol.24 (12), p.2777-2780
Main Authors: Zoidl, Manuel, Müller, Bernhard, Torvisco, Ana, Tysoe, Christina, Benazza, Mohamed, Siriwardena, Aloysius, Withers, Stephen G., Wrodnigg, Tanja M.
Format: Article
Language:English
Subjects:
Aza Compounds - chemistry
C-1-cyano-iminosugar building blocks
Crystallography, X-Ray
Glucocerebrosidase
Glycosidase inhibitor
Imino Pyranoses - chemical synthesis
Imino Pyranoses - chemistry
Iminoalditol
Magnetic Resonance Spectroscopy
Molecular Structure
Nitriles - chemistry
Staudinger/aza Wittig Strecker multicomponent reaction
Stereoisomerism
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Summary:The Staudinger/aza Wittig/Strecker (SAWS) multicomponent reaction (MCR) sequence applied to azidodeoxy carbohydrate substrates leads smoothly in good yield and with excellent stereoselectivity to versatile C-glycosyl iminoalditol analogues which prove useful as building blocks en route to functionalized C-glycosyl iminoalditols able to inhibit human lysosomal β-glucocerebrosidase. A new Staudinger/aza Wittig/Strecker multicomponent reaction sequence to C-1-cyano iminoalditols has been developed. When applied to 5-azidodeoxy-d-xylose and -d-glucose as substrates the method leads smoothly in good yield and with excellent stereoselectivity to respectively, 1,5-dideoxy-1,5-imino-d-idurono nitrile and 2,6-didesoxy-2,6-imino-d-glycero-d-ido-heptononitrile.
ISSN:0960-894X
1464-3405
DOI:10.1016/j.bmcl.2014.03.069