Issue 0, 1983
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Functionalised carbocycles from carbohydrates. Part 2. The synthesis of 3-oxa-2-azabicyclo[3.3.0]octanes. X-Ray crystal structure of (1R,5S)-6-exo,7-endo,8-exo-triacetoxy-N-methyl-4-endo-phenylthio-3-oxa-2-azabicyclo[3.3.0]octane

Robert J. Ferrier,   Richard H. Furneaux,   Petpiboon Prasit,   Peter C. Tyler,   Kevin L. Brown,   Graeme J. Gainsford  and  Justin W. Diehl  

Abstract

Treatment of various 6-bromo-6-deoxy- and 6-deoxy-6-iodo-D-glucopyranosyl compounds with zinc in ethanol affords acyclic 5,6-dideoxy-D-xylo-hex-5-enoses which have been converted into 3-oxa-2-azabicyclo[3.3.0]octanes containing functional groups which permit specific reactions at C-4 and at C-8. One such compound (10a) was characterised by X-ray diffraction analysis. Aspects of the chemistry of 4-hydroxy derivatives are described including their conversion into novel functionalised cyclopentanes.

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Article information

DOI
https://doi.org/10.1039/P19830001621
Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1983, 1621-1628

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Functionalised carbocycles from carbohydrates. Part 2. The synthesis of 3-oxa-2-azabicyclo[3.3.0]octanes. X-Ray crystal structure of (1R,5S)-6-exo,7-endo,8-exo-triacetoxy-N-methyl-4-endo-phenylthio-3-oxa-2-azabicyclo[3.3.0]octane

R. J. Ferrier, R. H. Furneaux, P. Prasit, P. C. Tyler, K. L. Brown, G. J. Gainsford and J. W. Diehl, J. Chem. Soc., Perkin Trans. 1, 1983, 1621 DOI: 10.1039/P19830001621

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