86420-66-8

Basic information

• Product Name: methyl 4,6-O-benzylidene-α-D-galactopyranoside 2,3-di-O-p-toluenesulfonate
• Synonyms: methyl 4,6-O-benzylidene-α-D-galactopyranoside 2,3-di-O-p-toluenesulfonate
• CAS NO: 86420-66-8
• Molecular Weight: 590.672
• Mol File: 86420-66-8.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: methyl 4,6-O-benzylidene-α-D-galactopyranoside 2,3-di-O-p-toluenesulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 4,6-O-benzylidene-α-D-galactopyranoside 2,3-di-O-p-toluenesulfonate(86420-66-8)
• EPA Substance Registry System: methyl 4,6-O-benzylidene-α-D-galactopyranoside 2,3-di-O-p-toluenesulfonate(86420-66-8)

Safety Data

• Hazardous Substances Data: 86420-66-8(Hazardous Substances Data)

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 71117-36-7 methyl 4,6-O-(S)-benzylidene-β-D-galactopyranoside 
• 1824-94-8 methyl beta-D-galactopyranoside 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 64552-06-3 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 

Downstream Products

• 86420-78-2 methyl 2,3-anhydro-4,6-O-benzylidene-β-D-talopyranoside 
• 130272-53-6 methyl 4,6-O-benzylidene-2,3-dideoxy-β-D-threo-hex-2-enoside 
• 2880-96-8 methyl 2,3-anhydro-4,6-dioxabenzylidene-α-D-talopyranose 
• 2880-96-8 methyl 2,3-anhydro-4,6-dioxabenzylidene-α-D-gulopyranose 
• 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 
• 2484-81-3 methyl-[O²-acetyl-3-acetylamino-O⁴,O⁶-((S)-benzylidene)-3-deoxy-β-D-idopyranoside] 
• 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.

Stereochemical dependence of the mechanism of deoxygenation, with lithium triethylborohydride, in 4,6-O-benzylidenehexopyranoside p-toluenesulfonates

Lithium triethylborohydride was shown to react with methyl 4,6-O-benzylidene-α-D-hexopyranoside 2- and 3-tosylates, and 2,3-ditosylates, in the manno, allo, and altro configurational series both by O-S fission (O-desulfonylation) and by C-O fission (C-desulfonyloxylation), to produce carbinol and deoxy functions, respectively.The results were compared with those previously obtained with the corresponding gluco and galacto isomers, and the degree of facility of the cleavage reactions was seen to depend on the position of the sulfonic ester groups and the overall configuration of the molecules.The mechanism of reductive desulfonyloxylation also depended on configuration and was demonstrated to involve intermediary epoxide formation or displacement by internal hydride shift as the principal paths; competing elimination and direct nucleophilic displacement were found to occur in the allo series, whereas reduction accompanied by ring contraction has thus far been encountered only in the conformationally less constrained, cis-fused acetal system of the galacto series.Like the borohydride reagent, lithium aluminum hydride was found to react (though much more slowly) with the altro 2,3-ditosylate by the epoxide-mediated mechanism, although the latter hydride is known to desulfonyloxylate the α-D-gluco-isomer by a different, intramolecular reduction mechanism.