Exploitation of in Situ Generated Sugar-Based Olefin Keto-Nitrones: Synthesis of Carbocycles, Heterocycles, and Nucleoside Derivatives
IR@IICB: CSIR-Indian Institute of Chemical Biology, Kolkata
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| Title |
Exploitation of in Situ Generated Sugar-Based Olefin Keto-Nitrones: Synthesis of Carbocycles, Heterocycles, and Nucleoside Derivatives
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| Creator |
Das, Soumendra Nath
Chowdhury, Arpan Tripathi, Neha Jana, Prithwish K Mandal, Sukhendu B |
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| Subject |
Chemistry
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| 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.
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| Publisher |
American Chemical Society
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| Date |
2015
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| Type |
Article
PeerReviewed |
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| Format |
application/pdf
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| 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. |
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| Relation |
http://dx.xoi.org/10.1021/jo502672x
http://www.eprints.iicb.res.in/2232/ |
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