2-Aza-3-oxabicyclo[2.2.1]heptene hydrochloride: an exceptionally versatile synthon for carbocyclic sugars and nucleosides

Ranganathan, Subramania ; Shaji George, K. (1997) 2-Aza-3-oxabicyclo[2.2.1]heptene hydrochloride: an exceptionally versatile synthon for carbocyclic sugars and nucleosides Tetrahedron, 53 (9). pp. 3347-3362. ISSN 0040-4020

Full text not available from this repository.

Official URL: http://linkinghub.elsevier.com/retrieve/pii/S00404...

Related URL: http://dx.doi.org/10.1016/S0040-4020(97)00057-4

Abstract

The transformation of cyclopentadiene to 5'-desmethylene 1'-aza carbocyclic sugars has been achieved in four steps: 1. Cycloaddition of chloronitrosocyclohexane to 2-aza-3-oxabicyclo[2.2.1]heptene hydrochloride in EtOH-Et2O, 2. Nitrogen functiona-lization, 3. cis hydroxylation and 4. N---O bond cleavage. The protocols provided enable practical access to a range of 5'-desmethylene carbocyclic sugar analogs whose utility has been illustrated with synthesis of a novel 5'-desmethylene analog of aristeromycin.

Item Type:Article
Source:Copyright of this article belongs to Elsevier Science.
ID Code:48874
Deposited On:20 Jul 2011 06:50
Last Modified:20 Jul 2011 06:50

Repository Staff Only: item control page