Bicyclic Nucleoside Analogues from D-glucose: Synthesis of Chiral As Well As Racemic 1,4-Dioxepane Ring-Fused Derivatives.
IR@IICB: CSIR-Indian Institute of Chemical Biology, Kolkata
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| Title |
Bicyclic Nucleoside Analogues from D-glucose: Synthesis of Chiral As Well As Racemic 1,4-Dioxepane Ring-Fused Derivatives.
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| Creator |
Tripathi, Subhankar
Maiti, Joy Krishna Achari, Basudeb Mandal, Sukhendu B |
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| Subject |
Chemistry
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| Description |
Abstract—The dioxepanofuranose derivatives 4 and 12, obtained through the cyclization of the 3-(2-hydroxyethyl) ether of a D-xylo-pentodialdose derivative, were appropriately functionalized and elaborated to the first examples of the new class of 30-O, and 50-O-bicyclic nucleoside analogues 9, 10, and 14 with a fused seven-membered ring. Reactions carried out through the intermediacy of the D-xylo-pentodialdose derivative 5 yielded racemic products, while prior protection of the 4-formyl group (as in 7) before deprotection of the 1,2-hydroxyl groups led to optically active analogues.
� 2005 Elsevier Ltd. All rights reserved.
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| Date |
2005
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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/1086/1/CARBOHYDRATE_RESEARCH%2C__340_(_6)%2C___Pages_1081%2D1087_[63].pdf
Tripathi, Subhankar and Maiti, Joy Krishna and Achari, Basudeb and Mandal, Sukhendu B (2005) Bicyclic Nucleoside Analogues from D-glucose: Synthesis of Chiral As Well As Racemic 1,4-Dioxepane Ring-Fused Derivatives. Carbohydrate Research, 340 (6). pp. 1081-1087. |
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| Relation |
http://dx.doi.org/10.1016/j.carres.2005.02.007
http://www.eprints.iicb.res.in/1086/ |
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