Ceric ammonium nitrate-catalyzed azidation of 1,2-anhydro sugars: application in the synthesis of structurally diverse sugar-derived morpholine 1,2,3-triazoles and 1,4-oxazin-2-ones

Suman Reddy, Y. ; John Pal, A. P. ; Gupta, Preeti ; Ansari, Alafia A. ; Vankar, Yashwant D. (2011) Ceric ammonium nitrate-catalyzed azidation of 1,2-anhydro sugars: application in the synthesis of structurally diverse sugar-derived morpholine 1,2,3-triazoles and 1,4-oxazin-2-ones Journal of Organic Chemistry, 76 (15). pp. 5972-5984. ISSN 0022-3263

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Official URL: http://pubs.acs.org/doi/abs/10.1021/jo200260w

Related URL: http://dx.doi.org/10.1021/jo200260w

Abstract

Azidation of 1,2-anhydro sugars with NaN3 in CH3CN by using a catalytic amount of ceric ammonium nitrate has been accomplished in a regio- and stereoselective manner. Various 1,2-anhydro sugars produced 2-hydroxy-1-azido sugars in good yields which, in turn, were converted to structurally diverse sugar-derived morpholine triazoles and sugar oxazin-2-ones. These sugar derivatives were tested against various commercially available glycosidases, and two of them were found to be active in the micromolar range.

Item Type:Article
Source:Copyright of this article belongs to American Chemical Society.
ID Code:58187
Deposited On:31 Aug 2011 06:48
Last Modified:31 Aug 2011 06:48

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