86420-68-0

Basic information

• Product Name: methyl 4,6-O-benzylidene-α-D-galactopyranoside 3-O-p-toluenesulfonate
• Synonyms: methyl 4,6-O-benzylidene-α-D-galactopyranoside 3-O-p-toluenesulfonate
• CAS NO: 86420-68-0
• Molecular Weight: 436.483
• Mol File: 86420-68-0.mol

Chemical Properties

• CAS DataBase Reference: methyl 4,6-O-benzylidene-α-D-galactopyranoside 3-O-p-toluenesulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 4,6-O-benzylidene-α-D-galactopyranoside 3-O-p-toluenesulfonate(86420-68-0)
• EPA Substance Registry System: methyl 4,6-O-benzylidene-α-D-galactopyranoside 3-O-p-toluenesulfonate(86420-68-0)

Safety Data

• Hazardous Substances Data: 86420-68-0(Hazardous Substances Data)

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 64552-06-3 methyl 4,6-O-benzylidene-α-D-galactopyranoside 
• 28538-12-7 methyl 2-O-benzoyl-4,6-O-benzylidene-3-O-p-tolylsulfonyl-α-D-allopyranoside 
• 3396-99-4 methyl α-D-galactopyranoside 
• 56253-26-0 methyl 2-O-benzoyl-4,6-O-benzylidene-α-D-allopyranoside 

Downstream Products

• 2880-96-8 methyl 2,3-anhydro-4,6-dioxabenzylidene-α-D-gulopyranose 
• 28538-12-7 methyl-[O²-benzoyl-O⁴,O⁶-((S)-benzylidene)-O³-(toluene-4-sulfonyl)-α-D-galactopyranoside] 
• 129831-92-1 Methyl 4,6-O-benzylidene-2-O-methyl-3-O-p-tolylsulfonyl-α-D-galactopyranoside 
• 74560-62-6 methyl 4,6-O-(S)-benzylidene-2-methyl-α-D-idopyranoside 
• 6748-86-3 methyl 4,6-O-benzylidene-3-O-p-tolylsulfonyl-α-D-allopyranoside 
• 16697-41-9 methyl-[O⁴,O⁶-((S)-benzylidene)-O³,S-dimethyl-2-thio-α-D-idopyranoside] 
• 79015-45-5 methyl-[O⁴,O⁶((S)-benzylidene)-S-methyl-2-thio-α-D-idopyranoside] 
• 129831-91-0 methyl 4,6-O-(S)-benzylidene-2-O-methyl-α-D-galactopyranoside 
• 21090-92-6 methyl-[O⁴,O⁶-((S)-benzylidene)-O³-methyl-α-D-xylo-2-deoxy-hexopyranoside] 
• 6752-48-3 methyl-[O⁴,O⁶-((S)-benzylidene)-α-D-xylo-2-deoxy-hexopyranoside] 

Relevant articles and documents

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.

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.