Synthesis of fused oxa-aza spiro sugars from D-glucose-derived δ-lactone as glycosidase inhibitors

John Pal, A. P. ; Gupta, Preeti ; Suman Reddy, Y. ; Vankar, Yashwant D. (2010) Synthesis of fused oxa-aza spiro sugars from D-glucose-derived δ-lactone as glycosidase inhibitors European Journal of Organic Chemistry, 2010 (36). pp. 6957-6966. ISSN 1434-193X

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Official URL: http://onlinelibrary.wiley.com/doi/10.1002/ejoc.20...

Related URL: http://dx.doi.org/10.1002/ejoc.201001102

Abstract

Four conformationally constrained fused oxa-aza spiro sugars have been synthesized from perbenzylated D-gluconolactone involving C-glycosylation of ketoses by using Me3SiCN, ring-closing metathesis, and diastereoselective dihydroxylation as key steps. Two of the four spiro sugars were found to be highly selective but moderate inhibitors of α-mannosidase.

Item Type:Article
Source:Copyright of this article belongs to John Wiley and Sons.
Keywords:Glycosylation; Metathesis; Dihydroxylation; Spiro Compounds; Azasugars; Enzyme Inhibitors
ID Code:58168
Deposited On:31 Aug 2011 06:42
Last Modified:31 Aug 2011 06:42

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