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
View Archive Info| Field | Value | |
| 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
Maity, Joy Krishna Achari, Basudeb Mandal, Sukhendu B |
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| Subject |
Chemistry
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| Description |
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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| Publisher |
Elsevier
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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/365/1/CARBOHYDRATE_RESEARCH_340(_6_)_1081%2D1087_;2005[63].pdf
Tripathi, Subhankar and Maity, 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. 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/365/ |
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