Concise and practical synthesis of (2 S,3 R,4 R,5 R) and (2 S,3 R,4 R,5 S)-1,6-dideoxy-1,6-iminosugars

The syntheses of (2 S,3 R,4 R,5 R) and (2 S,3 R,4 R,5 S)-1,6-dideoxy-1,6 iminosugars 1a and 1b , respectively, from d-glucose are described. The key transformations in this reaction sequence include regio-selective epoxide ring opening with N-benzylamine followed by intramolecular reductive aminatio...

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Bibliographic Details
Published in:Tetrahedron 2003-03, Vol.59 (11), p.1873-1876
Main Authors: Tilekar, Jayant N, Patil, Nitin T, Jadhav, Harishchandra S, Dhavale, Dilip D
Format: Article
Language:English
Subjects:
carbohydrates
d-glucoazepane
enzyme inhibitors
imino sugars
l-idoazepane
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Summary:The syntheses of (2 S,3 R,4 R,5 R) and (2 S,3 R,4 R,5 S)-1,6-dideoxy-1,6 iminosugars 1a and 1b , respectively, from d-glucose are described. The key transformations in this reaction sequence include regio-selective epoxide ring opening with N-benzylamine followed by intramolecular reductive amination of amino-aldehyde. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(03)00177-7