Peer-Reviewed Journal Details
Mandatory Fields
Enright, PM,Tosin, M,Nieuwenhuyzen, M,Cronin, L,Murphy, PV
2002
May
Journal Of Organic Chemistry
A study of the epoxidation of 6-deoxyhex-5-enopyranosides. 1,5-dicarbonyl derivatives and novel synthetic routes to D-xylo-hexos-5-ulose and D-lyxo-hexos-5-ulose
Published
()
Optional Fields
DOUBLE REDUCTIVE AMINATION BETA-D-GLUCOPYRANOSE CARBOHYDRATE-DERIVATIVES COMPLEX SACCHARIDES D-GALACTOSE ISOMERIC COMPOSITION PHOTO-BROMINATION AQUEOUS-SOLUTION IN-SITU CONVERSION
67
3733
3741
The work described deals with the isolation and characterization of epoxides from 6-deoxyhex-5-enopyranosides and preliminary exploration of their synthetic potential. Prolonged epoxidation reaction times led to their hydrolysis in situ and gave novel protected D-hexos-5-ulose derivatives (sugar 1,5-dicarbonyls). Some reactions of the hexos-5-uloses were studied, and in some cases septanoside (seven-membered-ring saccharide) derivatives were isolated. Novel routes to D-xylo-hexos-5-ulose and D-lyxo-hexos-5-ulose, of interest as intermediates in the synthesis and biosynthesis of inositols and aza sugars, are also described. The structures of the epoxides and novel hexos-5-uloses were established by NMR and X-ray crystallographic methods.
DOI 10.1021/jo016378c
Grant Details
Publication Themes