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Synthesis of Oxepane Ring Containing Monocyclic, Conformationally Restricted Bicyclic and Spirocyclic Nucleosides from D-Glucose: A Cycloaddition Approach

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Title Synthesis of Oxepane Ring Containing Monocyclic, Conformationally Restricted Bicyclic and Spirocyclic Nucleosides from D-Glucose: A Cycloaddition Approach
 
Creator Tripathi, Subhankar
Roy, Biswajit G
Drew, Michael G. B
Achari, Basudeb
Mandal, Sukhendu B
 
Subject Chemistry
 
Description Carbohydrate-derived substrates having (i) C-5 nitrone and
C-3-O-allyl, (ii) C-4 vinyl and a C-3-O-tethered nitrone, and (iii) C-5 nitrone and C-4-allyloxymethyl generated tetracyclic isoxazolidinooxepane/-pyran ring systems upon intramolecular nitrone cycloaddition reactions. Deprotection of the 1,2- acetonides of these derivatives followed by introduction of uracil base via Vorbru¨ggen reaction condition and cleavage of the isooxazolidine rings as well as of benzyl groups by transfer hydrogenolysis yielded an oxepane ring containing bicyclic and spirocyclic nucleosides. The corresponding oxepane based nucleoside analogues were prepared by cleavage of isoxazolidine and furanose rings, coupling of the generated amino functionalities with 5-amino-4,6-dichloropyrimidine,
cyclization to purine rings, and finally aminolysis.
 
Date 2007
 
Type Article
PeerReviewed
 
Format application/pdf
 
Identifier http://www.eprints.iicb.res.in/267/1/JOURNAL_OF_ORGANIC_CHEMISTRY%2C72_(19)%2C7427%2D7430%2C2008[35].pdf
Tripathi, Subhankar and Roy, Biswajit G and Drew, Michael G. B and Achari, Basudeb and Mandal, Sukhendu B (2007) Synthesis of Oxepane Ring Containing Monocyclic, Conformationally Restricted Bicyclic and Spirocyclic Nucleosides from D-Glucose: A Cycloaddition Approach. The Journal of Organic Chemistry, 72 (19). pp. 7427-7430.
 
Relation http://dx.doi.org/10.1021/jo070846m CCC: $37.00
http://www.eprints.iicb.res.in/267/