129831-96-5

Basic information

• Product Name: methyl 4,6-O-(S)-benzylidene-3-O-methyl-β-D-idopyranoside
• Synonyms: methyl 4,6-O-(S)-benzylidene-3-O-methyl-β-D-idopyranoside
• CAS NO: 129831-96-5
• Molecular Weight: 296.32
• Mol File: 129831-96-5.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: methyl 4,6-O-(S)-benzylidene-3-O-methyl-β-D-idopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 4,6-O-(S)-benzylidene-3-O-methyl-β-D-idopyranoside(129831-96-5)
• EPA Substance Registry System: methyl 4,6-O-(S)-benzylidene-3-O-methyl-β-D-idopyranoside(129831-96-5)

Safety Data

• Hazardous Substances Data: 129831-96-5(Hazardous Substances Data)

Upstream product

• 86420-78-2 methyl 2,3-anhydro-4,6-O-benzylidene-β-D-talopyranoside 
• 6748-86-3 methyl 4,6-O-benzylidene-β-D-galactopyranoside 2,3-di-O-p-toluenesulfonate 
• 67-56-1 methanol 
• 1824-94-8 methyl beta-D-galactopyranoside 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 71117-36-7 methyl 4,6-O-(S)-benzylidene-β-D-galactopyranoside 
• 81825-61-8 methyl 2-O-acetyl-4,6-O-benzylidene-3-O-methyl-α-D-galactopyranoside 

Downstream Products

• 113159-07-2 methyl 3-O-methyl-α-D-idopyranoside 
• 3013-58-9 methyl 4,6-O-(S)-benzylidene-2,3-di-O-methyl-β-D-idopyranoside 
• 81825-63-0 methyl 2-O-benzyl-4,6-O-benzylidene-3-O-methyl-α-D-galactopyranoside 

Relevant articles and documents

Evidence of cation-coordination involvement in directing the regioselective di-inversion reaction of vicinal di-sulfonate esters

Direct evidence has been obtained to confirm the unusual nucleophilic attack of an alkoxide at the S-center of sp3-hybridized sulfonyl esters. The unusual reaction pathway leads to S-O bond scission which is crucial for the regio- and stereoselective conversion of 2,3-di-O-sulfonates of 4,6-O-benzylidene-β-d-galactopyranosides into β-d-idopyranosides. In addition, strong evidence has been provided to clarify the role of the alkali counter-cation in the transformation. The cation is believed to influence the reaction rate via coordination to an oxygen in the sulfonate ester; the presence of a neighboring ring oxygen oriented in a cis-relationship greatly enhances reactivity of the sulfonyl ester.