156924-97-9

Basic information

• Product Name: methyl 4,6-O-benzylidene-α-D-galactopyranoside 3-O-benzoate
• Synonyms: methyl 4,6-O-benzylidene-α-D-galactopyranoside 3-O-benzoate
• CAS NO: 156924-97-9
• Molecular Weight: 372.418
• Mol File: 156924-97-9.mol

Chemical Properties

• CAS DataBase Reference: methyl 4,6-O-benzylidene-α-D-galactopyranoside 3-O-benzoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 4,6-O-benzylidene-α-D-galactopyranoside 3-O-benzoate(156924-97-9)
• EPA Substance Registry System: methyl 4,6-O-benzylidene-α-D-galactopyranoside 3-O-benzoate(156924-97-9)

Safety Data

• Hazardous Substances Data: 156924-97-9(Hazardous Substances Data)

Upstream product

• 100-39-0 benzyl bromide 
• 64552-06-3 methyl 4,6-O-benzylidene-α-D-galactopyranoside 
• 98-88-4 benzoyl chloride 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 3396-99-4 methyl α-D-galactopyranoside 
• 100-44-7 benzyl chloride 

Downstream Products

• 1013654-14-2 methyl (N-acetyl-2-amino-2,3-N,O-carbonyl-4,6-diacetyl-2-deoxy-β-D-glucopyranosyl)-(1->2)-3-O-benzyl-4,6-O-benzylidene-α-D-galactopyranoside 
• 1013654-31-3 methyl (N-acetyl-2-amino-2,3-N,O-carbonyl-4,6-diacetyl-2-deoxy-α-D-glucopyranosyl)-(1->2)-3-O-benzyl-4,6-O-benzylidene-α-D-galactopyranoside 
• 1199797-30-2 C₂₁H₂₂O₆ 
• 1363732-67-5 methyl 3,4-di-O-benzoyl-2-O-benzyl-α-L-fucopyranosyl-(1->2)-3-O-benzyl-4,6-O-benylidene-α-D-galactopyranoside 
• 1337979-74-4 methyl 3,4-di-O-benzoyl-2-O-benzyl-β-L-fucopyranosyl-(1->2)-3-O-benzyl-4,6-O-benylidene-α-D-galactopyranoside 
• 1393354-73-8 methyl 2-O-benzyl-3-O-acetyl-4,6-O-benzylidene-α-D-galactopyranoside 

Relevant articles and documents

Organotin-catalyzed regioselective benzylation of carbohydrate trans-diols

A convenient approach to regioselective benzylation of carbohydrate trans-diols was developed, where 0.1 equiv. of Bu2SnCl2 and 0.1 equiv. of TBABr were used as the catalysts and 2.0 equiv. of BnCl was used as the benzylation reagent. In most cases, similar or better benzylation regioselectivities and isolated yields were obtained by using catalytic amounts of Bu2SnCl2, rather than stoichiometric amounts of organotin reagents required.

An Iron(III) Catalyst with Unusually Broad Substrate Scope in Regioselective Alkylation of Diols and Polyols

In this study, [Fe(dibm)3] (dibm=diisobutyrylmethane) is shown to have unusually broad scope as a catalyst for the selective monoalkylation of a diverse set of 1,2- and 1,3-diol-containing structures. The mechanism is proposed to proceed via a cyclic dioxolane-type intermediate, formed between the iron(III) species and two adjacent hydroxyl groups. This approach represents the first transition-metal catalysts that are able to replace stoichiometric amounts of organotin reagents in regioselective alkylation. The reactions generally lead to very high regioselectivities and high yields, on par with, or better than, previous methods used for regioselective alkylation.

Fluorine-directed β-galactosylation: Chemical glycosylation development by molecular editing

Validation of the 2-fluoro substituent as an inert steering group to control chemical glycosylation is presented. A molecular editing study has revealed that the exceptional levels of diastereocontrol in glycosylation processes by using 2-fluoro-3,4,6-tri-O-benzyl glucopyranosyl trichloroacetimidate (TCA) scaffolds are a consequence of the 2R,3S,4S stereotriad. This study has also revealed that epimerization at C4, results in a substantial enhancement in β-selectivity (up to β/α 300:1). Copyright

Monoalkylation of tributyltin activated methyl 4,6-O-benzylidene-α-D-gluco- and -galactopyranosides

Monoalkylation of methyl 4,6-O-benzylidene-α-D-gluco- and galactopyranosides could be carried out in good yields using bis(tributyltin) oxide. Regioselectivity, giving predominant 2-substitution, was excellent in the case of D-glucopyranoside. The ratio o

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.