Thio-sugars. Part 5: From d-glucal to 3-deoxy-(1→2)-2- S-thiodisaccharides through isolevoglucosenone—a simple approach

A new synthesis of isolevoglucosenone and its stereoselective functionalization into 3-deoxy-(1-2)-2- S-thiodisaccharides is described. The base-catalyzed conjugate addition of 1-thiosugars to isolevoglucosenone followed by the reduction of the C-4 keto function constitute a new two-step general app...

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Bibliographic Details
Published in:Tetrahedron: asymmetry 2000-02, Vol.11 (2), p.519-532
Main Authors: Witczak, Zbigniew J, Chen, Hong, Kaplon, Peter
Format: Article
Language:English
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Summary:A new synthesis of isolevoglucosenone and its stereoselective functionalization into 3-deoxy-(1-2)-2- S-thiodisaccharides is described. The base-catalyzed conjugate addition of 1-thiosugars to isolevoglucosenone followed by the reduction of the C-4 keto function constitute a new two-step general approach to these classes of biologically important thio-sugars.
ISSN:0957-4166
1362-511X
DOI:10.1016/S0957-4166(99)00567-4