137013-05-9

Upstream product

• 80564-48-3 methyl 3,6-anhydro-2,4-di-O-acetyl-α-D-mannopyranoside 
• 98-59-9 p-toluenesulfonyl chloride 
• 15814-56-9 methyl 3,6-anhydro-α-D-mannopyranoside 
• 100109-50-0 methyl-[O³,O⁴-diacetyl-O²,O⁶-bis-(toluene-4-sulfonyl)-β-D-glucopyranoside] 
• 13407-62-0 methyl-[O²-(toluene-4-sulfonyl)-3,6-anhydro-β-D-glucopyranoside] 
• 3056-46-0 methyl 3,6-anhydro-β-D-glucopyranoside 

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.

Bis-deoxygenation of methyl 3,6-anhydro-D-pyranosides

The synthesis and radical reduction of thiocarbonyl derivatives of methyl 3,6-anhydro pyranosides has been studied in the α-D-gluco, α-D-manno and β-D-galacto series. A cyclic intermediate is proposed to explain the fact that bis-deoxygenation only occurr