A Synthetic Route to Fully Substituted Chiral Cyclopentylamine Derivatives:Precursors of Carbanucleosides
IR@IICB: CSIR-Indian Institute of Chemical Biology, Kolkata
View Archive Info| Field | Value | |
| 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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