Synthesis of a New Family of Aminocyclitols from D-(-)-Quinic Acid

In continuation of our interest in the synthesis of glycosidase inhibitors, we report herein an efficient synthesis of three new polyhydroxylated amino cyclohexane derivatives (aminocyclitols) that may potentially possess important biological activities. The key step involved the highly stereoselect...

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Bibliographic Details
Published in:Synthetic communications 2008-11, Vol.38 (23), p.4139-4149
Main Authors: Shih, Tzenge-Lien, Li, Heng-Yi, Ke, Ming-Shin, Kuo, Wei-Shen
Format: Article
Language:English
Subjects:
Aminocyclitol
dihydroxylation
quinic acid
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Summary:In continuation of our interest in the synthesis of glycosidase inhibitors, we report herein an efficient synthesis of three new polyhydroxylated amino cyclohexane derivatives (aminocyclitols) that may potentially possess important biological activities. The key step involved the highly stereoselective dihydroxylation of protected azido cyclohexene derivatives 5, 9, and 15, which were easily red from D-(-)-quinic acid. The subsequent hydrogenation step was conducted under acidic conditions to provide the target molecules in an efficient manner with high overall yields.
ISSN:0039-7911
1532-2432
DOI:10.1080/00397910802281429