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Exploitation of in Situ Generated Sugar-Based Olefin Keto-Nitrones: Synthesis of Carbocycles, Heterocycles, and Nucleoside Derivatives

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Title Exploitation of in Situ Generated Sugar-Based Olefin Keto-Nitrones: Synthesis of Carbocycles, Heterocycles, and Nucleoside Derivatives
 
Creator Das, Soumendra Nath
Chowdhury, Arpan
Tripathi, Neha
Jana, Prithwish K
Mandal, Sukhendu B
 
Subject Chemistry
 
Description Application of intramolecular 1,3-dipolar nitrone
cycloaddition reaction on carbohydrate-derived precursors
containing an olefin functionality at C-1 or C-3 or C-5 and a nitrone moiety at C-2 or C-3 as appropriate has resulted in the formation of structurally new cycloaddition products containing furanose-fused oxepane, thiepane, azepane, cyclopentane, cycloheptane, tetrahydrofuran, and pyranose-fused tetrahydrofuran rings. The structure and stereochemistry of these products have been characterized by spectral as well as single-crystal X-ray analyses. Two of the compounds have been transformed to the bicyclic nucleoside derivatives applying Vorbrüggen reaction
conditions.
 
Publisher American Chemical Society
 
Date 2015
 
Type Article
PeerReviewed
 
Format application/pdf
 
Identifier http://www.eprints.iicb.res.in/2232/1/JOURNAL_OF_ORGANIC_CHEMISTRY__V._80(_2_)_1136%2D1148_;2015[79].pdf
Das, Soumendra Nath and Chowdhury, Arpan and Tripathi, Neha and Jana, Prithwish K and Mandal, Sukhendu B (2015) Exploitation of in Situ Generated Sugar-Based Olefin Keto-Nitrones: Synthesis of Carbocycles, Heterocycles, and Nucleoside Derivatives. The Journal of Organic Chemistry, 80 (2). pp. 1136-1148.
 
Relation http://dx.xoi.org/10.1021/jo502672x
http://www.eprints.iicb.res.in/2232/