145525-79-7

Upstream product

• 3587-60-8 Benzyloxymethyl chloride 
• 3162-96-7 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside 

Downstream Products

• 145525-80-0 (2R,4aR,6S,7S,8aR)-7-Benzyloxymethoxy-6-methoxy-2-phenyl-tetrahydro-pyrano[3,2-d][1,3]dioxin-8-one 

Relevant academic research and scientific papers

Chemistry of oxo-sugars (1). Rearrangement of 2-oxoglycosides in pyridine: Evidence of intramolecular hydride shift

Methyl α- and β-D-arabinohexopyranosid-2-uloses rearranged, in pyridine, into methyl α- and β-D-ribohexopyranosid-3-uloses through intermediacy of methyl α- and β-D-arabinohexopyranosid-3-uloses, respectively, indicating that an intramolecular hydride shift is the initial reaction for rearrangement of 2-oxoglycosides.

Chemistry of oxo-sugars. (2). Regio- and stereo-selective synthesis of methyl D-hexopyranosiduloses and identification of their forms existing in solutions

Sixteen oxo derivatives of methyl D-hexopyranosides with various regio-and stereo-chemistries were selectively synthesized by direct oxidation of non-protected methyl glycosides by the bistributyltin oxide-bromine method or by oxidation of partially protected glycosides followed by deprotection. The forms of these oxoglycosides existing in pyridine-d5 and in H2O (D2O) were investigated by means of 13C-NMR spectroscopy, and it was found that interconversion between oxo and hydrate forms of oxoglycosides readily takes place.