126924-10-5

Upstream product

• 3162-96-7 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside 

Downstream Products

• 1227741-74-3 (E/Z)-methyl 4,6-O-benzylidene-2-deoxy-2-(2-carbamothioylhydrazono)-α-D-arabino-hexopyranoside 
• 1227741-72-1 methyl 4,6-O-benzylidenespiro[2-deoxy-α-D-arabino-hexopyranoside-2,2'-imidazolidine] 
• 1227741-73-2 methyl 4,6-O-benzylidenespiro-3',4',5',6'-tetrahydro-1'H-spiro-[2-deoxy-α-D-arabino-hexopyranoside-2,2'-pyrimidine] 
• 6748-94-3 methyl 2-acetamido-3-O-acetyl-4,6-di-O-benzylidene-2-deoxy-α-D-glucopyranoside 
• 128657-65-8 methyl 2-acetamido-3-O-acetyl-4,6-O-benzylidene-2-deoxy-α-D-mannopyranoside 
• 128583-64-2 methyl 4,6-O-benzylidene-α-D-arabino-2-hexulopyranoside O-methyloxime 
• 382591-40-4 methyl (2R,4aR,6S,9aR,9bS)-4,4a,6,8,9a,9b-hexahydro-6-methoxy-8-oxo-2-phenylfuro[2',3':4,5]pyrano[3,2-d]-1,3-dioxin-7-carboxylate 

Relevant academic research and scientific papers

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.

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.