439614-80-9

Upstream product

• 6304-96-7 methyl 2,3,4-tri-O-acetyl-6-deoxy-6-iodo-α-D-glucopyranoside 
• 6217-21-6 methyl 2,3,4-tri-O-acetyl-6-desoxy-α-D-xylo-hex-5-enopyranoside 
• 5155-46-4 methyl 6-iodo-6-deoxy-α-D-glucopyranoside 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 7154-66-7 2-bromobenzoic acid chloride 
• 316172-35-7 2,3,4-tri-O-benzyl-1,6-anhydro-β-L-idopyranos-5-ulo-5-hydrate 
• 85716-44-5 methyl 2,3,4-tri-O-benzyl-α-d-xylo-hex-5-enopyranoside 
• 20771-10-2 1-O-methyl-2,3,4-tri-O-trimethylsilyl-α-D-glucopyranoside 
• 59578-04-0 methyl 2,3,4-tri-O-trimethylsilyl-6-deoxy-6-iodo-α-D-glucopyranoside 
• 13265-83-3 methyl 6-deoxy-α-D-xylo-hex-5-enopyranoside 

Relevant academic research and scientific papers

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

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-xylohexos-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.