Synthesis of Oxepane Ring Containing Monocyclic, Conformationally Restricted Bicyclic and Spirocyclic Nucleosides from D-Glucose: A Cycloaddition Approach
IR@IICB: CSIR-Indian Institute of Chemical Biology, Kolkata
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| Title |
Synthesis of Oxepane Ring Containing Monocyclic, Conformationally Restricted Bicyclic and Spirocyclic Nucleosides from D-Glucose: A Cycloaddition Approach
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| Creator |
Tripathi, Subhankar
Roy, Biswajit G Drew, Michael G. B Achari, Basudeb Mandal, Sukhendu B |
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| Subject |
Chemistry
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| 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.
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| Date |
2007
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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/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. |
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| Relation |
http://dx.doi.org/10.1021/jo070846m CCC: $37.00
http://www.eprints.iicb.res.in/267/ |
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