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

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.