73111-72-5

Upstream product

• 100-39-0 benzyl bromide 
• 14897-47-3 methyl 3,4-di-O-isopropylidene-β-D-galactopyranoside 
• 1824-94-8 methyl beta-D-galactopyranoside 

Downstream Products

• 1063665-44-0 (1S,3a'R,6'R,7'R,7a'S)-7'-benzyloxy-2,2-dichloro-6'-methoxy-2',2'-dimethyltetrahydrospiro[cyclopropane-1,4'-[1,3]dioxolo[4,5-c]pyran] 
• 1063665-35-9 (3a'R,6'R,7'R,7a'S)-7'-benzyloxy-6'-methoxy-2',2'-dimethyltetrahydrospiro[cyclopropane-1,4'-[1,3]dioxolo[4,5-c]pyran] 
• 1063665-64-4 ethyl (1S,2R,3a'R,6'R,7'R,7a'S)-7'-benzyloxy-6'-methoxy-2',2'-dimethyltetrahydrospiro[cyclopropane-1,4'-[1,3]dioxolo[4,5-c]pyran]-2-carboxylate 
• 1063665-61-1 ethyl (1S,2S,3a'R,6'R,7'R,7a'S)-7'-benzyloxy-6'-methoxy-2',2'-dimethyltetrahydrospiro[cyclopropane-1,4'-[1,3]dioxolo[4,5-c]pyran]-2-carboxylate 
• 1063665-57-5 ethyl (1R,2R,3a'R,6'R,7'R,7a'S)-7'-benzyloxy-6'-methoxy-2',2'-dimethyltetrahydrospiro[cyclopropane-1,4'-[1,3]dioxolo[4,5-c]pyran]-2-carboxylate 
• 1063665-59-7 ethyl (1R,2S,3a'R,6'R,7'R,7a'S)-7'-benzyloxy-6'-methoxy-2',2'-dimethyltetrahydrospiro[cyclopropane-1,4'-[1,3]dioxolo[4,5-c]pyran]-2-carboxylate 

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.