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A synthetic route to fully substituted chiral cyclopentylamine derivatives: precursors of carbanucleosides

Mandal, S., Ghosh, R., Maity, J., Drew, M. and Achari, B. (2010) A synthetic route to fully substituted chiral cyclopentylamine derivatives: precursors of carbanucleosides. Synthesis-Stuttgart, 2010 (08). pp. 1303-1310. ISSN 0039-7881

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To link to this article DOI: 10.1055/s-0029-1218677

Abstract/Summary

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.

Item Type:Article
Refereed:Yes
Divisions:Faculty of Life Sciences > School of Chemistry, Food and Pharmacy > Department of Chemistry
ID Code:19609
Publisher:Georg Thieme Verlag

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