15384-63-1

Basic information

• Product Name: methyl 4,6-O-benzylidene-alpha-D-galactopyranoside, bis(toluene-p-sulphonate)
• Synonyms: methyl 4,6-O-benzylidene-alpha-D-galactopyranoside, bis(toluene-p-sulphonate);Methyl 4-O,6-O-(phenylmethylene)-2-O,3-O-bis(4-methylphenylsulfonyl)-α-D-galactopyranoside;Einecs 239-408-0
• CAS NO: 15384-63-1
• Molecular Formula: C28H30O10S2
• Molecular Weight: 590.6618
• EINECS: 239-408-0
• Mol File: 15384-63-1.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 737.8°Cat760mmHg
• Flash Point: 400°C
• Appearance: /
• Density: 1.43g/cm³
• CAS DataBase Reference: methyl 4,6-O-benzylidene-alpha-D-galactopyranoside, bis(toluene-p-sulphonate)(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 4,6-O-benzylidene-alpha-D-galactopyranoside, bis(toluene-p-sulphonate)(15384-63-1)
• EPA Substance Registry System: methyl 4,6-O-benzylidene-alpha-D-galactopyranoside, bis(toluene-p-sulphonate)(15384-63-1)

Safety Data

• Hazardous Substances Data: 15384-63-1(Hazardous Substances Data)

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 71117-36-7 methyl 4,6-O-(S)-benzylidene-β-D-galactopyranoside 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 1824-94-8 methyl beta-D-galactopyranoside 
• 4288-93-1 methyl 4,6-O-benzylidene-α-D-galactopyranoside 
• 3396-99-4 methyl α-D-galactopyranoside 
• 28538-12-7 methyl 2-O-benzoyl-4,6-O-benzylidene-3-O-p-tolylsulfonyl-α-D-allopyranoside 
• 6698-34-6 methyl 4,6-O-benzylidene-3-O-p-tolylsulfonyl-α-D-allopyranoside 
• 100-52-7 benzaldehyde 

Downstream Products

• 86420-78-2 methyl 2,3-anhydro-4,6-O-benzylidene-β-D-talopyranoside 
• 4288-93-1 methyl 4,6-O-benzylidene-α-D-galactopyranoside 
• 24332-87-4 methyl 4,6-O-benzylidene-3-deoxy-α-D-lyxo-hexopyranoside 
• 96530-45-9 methyl 3,5-O-benzylidene-2-deoxy-2-C-(hydroxymethyl)-α-D-lyxo-pentofuranoside 
• 18929-67-4 methyl 4-O-benzoyl-6-bromo-6-deoxy-2,3-di-O-tosyl-α-D-galactopyranoside 
• 40773-64-6 methyl 4,6-O-benzylidene-3-deoxy-ribo-hexopyranoside 
• 4153-17-7 methyl 4,6-O-benzylidene-α-D-allopyranoside 
• 34340-38-0 methyl 4,6-O-benzylidene-3-deoxy-α-D-erythro-hex-3-enopyranoside 
• 1385089-78-0 methyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-idopyranoside 
• 1385089-80-4 methyl 2,3-di-O-benzyl-β-D-idopyranoside 
• 1385089-83-7 methyl 3-O-allyl-2-O-benzyl-4,6-O-benzylidene-β-D-idopyranoside 
• 1385089-86-0 methyl 3-O-allyl-2-O-benzyl-β-D-idopyranoside 
• 1385089-75-7 methyl 3-O-allyl-4,6-O-benzylidene-β-D-idopyranoside 
• 2880-96-8 methyl 2,3-anhydro-4,6-O-benzylidene-β-D-gulopyranoside 

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.

Acetalation studies. Part VI. Concerning the effects of ultrasound on the benzylidenation of some alkyl D-glycopyranosides

The effects of ultrasound on conventional Freudenberg-type benzylidenation reactions of some alkyl D-glycopyranosides is described.A considerable enhancement in the rates of formation of the expected acetals was observed.The pure products were obtained in good yields.Some of the crude air-dried products were suitable for direct derivatisation.

SELECTIVE ESTERIFICATION OF METHYL 4,6-O-BENZYLIDENE-α-D- AND β-D-GALACTOPYRANOSIDE IN A CATALYTIC TWO-PHASE SYSTEM

Selective tosylation of methyl 4,6-O-benzylidene-α-D- (1) and β-D-galactopyranoside (8) in a catalytic two-phase system (CTP system) yields preferentially 2-O-p-toluenesulfonate and 3-O-p-toluenesulfonate, respectively.In the course of unimolar benzoylation of 1 and 8, under similar conditions, a migration of the acyl group takes place and an equilibrium mixture is obtained.Esterification of 1 and 8 with benzoyl chloride under CTP conditions, in presence of an aqueous sodium hydroxide solution, saturated with sodium perchlorate, afforded in preponderant yields 2-O-benzoate and 3-O-benzoate, respectively.