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Bicyclic nucleoside analogues from D-glucose: synthesis of chiral as well as racemic 1,4-dioxepane ring-fused derivatives

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Title Bicyclic nucleoside analogues from D-glucose: synthesis of chiral
as well as racemic 1,4-dioxepane ring-fused derivatives
 
Creator Tripathi, Subhankar
Maity, Joy Krishna
Achari, Basudeb
Mandal, Sukhendu B
 
Subject Chemistry
 
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.
 
Publisher Elsevier
 
Date 2005
 
Type Article
PeerReviewed
 
Format application/pdf
 
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.
 
Relation http://dx.doi.org/10.1016/j.carres.2005.02.007
http://www.eprints.iicb.res.in/365/