A Synthetic Route to Fully Substituted Chiral Cyclopentylamine Derivatives:Precursors of Carbanucleosides
EPrints@IICB
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Title |
A Synthetic Route to Fully Substituted Chiral Cyclopentylamine Derivatives:Precursors of Carbanucleosides
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Creator |
Ghosh, Ramprasad
Maity, Joy Krishna Drew, Michael G B Achari, Basudeb Mandal, Sukhendu B |
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Subject |
Chemistry
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Description |
Removal of silyl protection from D-glucose derived substrate 6 afforded 7, which upon acetonide deprotection followed by reaction with N-benzylhydroxylamine furnished two isomeric isoxazolidinocyclopentane derivatives via spontaneous cyclization of an in situ generated nitrone. The methyl xanthate derivative of the tertiary hydroxyl group of one isomer was isolated and subjected to radical deoxygenation reaction to form epimeric products, while with the other isomer it underwent spontaneous 1,2-elimination to form a mixture of the two possible endocyclic olefins. Hydrogenolytic cleavage of the isoxazolidine rings of the purified products followed by insertion of 5-amino-4-chloropyrimidine moiety and purine ring construction smoothly afforded structurally unique carbanucleoside analogues. Various spectroscopic methods on the synthesized compounds and X-ray analysis on one important intermediate were used to assign the structures and stereochemistry of the products. |
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Date |
2010
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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/26/1/SYNTHESIS%2DSTUTTGART_(8)_1303%2D1310_;2010[100].pdf
Ghosh, Ramprasad and Maity, Joy Krishna and Drew, Michael G B and Achari, Basudeb and Mandal, Sukhendu B (2010) A Synthetic Route to Fully Substituted Chiral Cyclopentylamine Derivatives:Precursors of Carbanucleosides. Synthesis (8). pp. 1303-1310. |
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Relation |
http://dx.doi.org/10.1055/s-0029-1218677
http://www.eprints.iicb.res.in/26/ |
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