3013-58-9

Basic information

• Product Name: methyl 4,6-O-benzylidene-2,3-di-O-methyl-α-D-galactopyranoside
• Synonyms: methyl 4,6-O-benzylidene-2,3-di-O-methyl-α-D-galactopyranoside
• CAS NO: 3013-58-9
• Molecular Weight: 310.347
• Mol File: 3013-58-9.mol
• Article Data: 26

Chemical Properties

• CAS DataBase Reference: methyl 4,6-O-benzylidene-2,3-di-O-methyl-α-D-galactopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 4,6-O-benzylidene-2,3-di-O-methyl-α-D-galactopyranoside(3013-58-9)
• EPA Substance Registry System: methyl 4,6-O-benzylidene-2,3-di-O-methyl-α-D-galactopyranoside(3013-58-9)

Safety Data

• Hazardous Substances Data: 3013-58-9(Hazardous Substances Data)

Upstream product

• 120408-72-2 Methyl 2,3-anhydro-4,6-O-(phenylmethylene)-β-D-allopyranoside 
• 3162-96-7 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside 
• 74-88-4 methyl iodide 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 50-99-7 D-glucose 
• 100-52-7 benzaldehyde 
• 3162-96-7 methyl 4,6-O-benzylidene-α-D-glucopyranoside 
• 77-78-1 dimethyl sulfate 
• 64552-06-3 methyl 4,6-O-benzylidene-α-D-galactopyranoside 
• 59-23-4 D-Galactose 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 3396-99-4 methyl α-D-galactopyranoside 
• 287191-51-9 methyl 4,6-O-benzylidene-β-D-idopyranoside 
• 6752-76-7 methyl 4,6-O-benzylidene-2-O-methyl-β-D-idopyranoside 

Downstream Products

• 106220-89-7 methyl 6-O-benzyl-2,3-di-O-methyl-α-D-glucopyranoside 
• 83075-53-0 methyl 4-O-benzyl-2,3-di-O-methyl-α-D-glucopyranoside 
• 56543-17-0 methyl 4-O-benzoyl-6-bromo-6-deoxy-2,3-di-O-methyl-α-D-glucopyranoside 
• 108223-99-0 methyl 4-O-benzyl-6-bromo-6-deoxy-4-O-(methoxyethoxymethyl)-2,3-di-O-methyl-α-D-glucopyranoside 
• 10227-29-9 methyl 2,3-di-O-methyl-α-D-glucopyranoside 
• 77454-10-5 methyl 4-O-benzoyl-6-bromo-6-deoxy-2,3-di-O-methyl-α-D-galactoside 
• 10227-29-9 methyl 2.3-di-O-methyl-α-D-galactopyranoside 
• 1064194-70-2 [(2R,3R,4S,5R,6S)-4,5,6-Trimethoxy-3-(phenyl-phenylsulfanyl-methoxy)-tetrahydro-pyran-2-yl]-methanol 
• 51517-51-2 methyl 6-O-benzoyl-2,3-di-O-methyl-α-D-glucopyranoside 
• 56543-16-9 methyl 4-O-benzoyl-2,3-di-O-methyl-α-D-glucopyranoside 
• 100-52-7 benzaldehyde 
• 53437-96-0 Benzoic acid (2R,3S,4S,5R,6S)-3-hydroxy-4,5,6-trimethoxy-tetrahydro-pyran-2-ylmethyl ester 
• 120104-39-4 Benzoic acid (2R,3S,4S,5R,6S)-2-hydroxymethyl-4,5,6-trimethoxy-tetrahydro-pyran-3-yl ester 
• 178319-42-1 methyl 4-O-benzyl-2,3,6-tri-O-methyl-α-D-glucopyranoside 

Relevant articles and documents

Establishment of Guidelines for the Control of Glycosylation Reactions and Intermediates by Quantitative Assessment of Reactivity

Stereocontrolled chemical glycosylation remains a major challenge despite vast efforts reported over many decades and so far still mainly relies on trial and error. Now it is shown that the relative reactivity value (RRV) of thioglycosides is an indicator for revealing stereoselectivities according to four types of acceptors. Mechanistic studies show that the reaction is dominated by two distinct intermediates: glycosyl triflates and glycosyl halides from N-halosuccinimide (NXS)/TfOH. The formation of glycosyl halide is highly correlated with the production of α-glycoside. These findings enable glycosylation reactions to be foreseen by using RRVs as an α/β-selectivity indicator and guidelines and rules to be developed for stereocontrolled glycosylation.

USE OF CO2 FOR THE SYNTHESIS OF CYCLIC GLYCOCARBONATES AND LINEAR POLYGLYCOCARBONATES BY POLYCONDENSATION FROM GLYCANS

Provided herein are methods for synthesizing cyclic carbonates, glycocarbonates, and polyglycocarbonates by reacting polyol glycans with carbon dioxide. Synthesis can include selective polycondensation of polyol glycan hydroxyl moieties.

Benzylidene Acetal Protecting Group as Carboxylic Acid Surrogate: Synthesis of Functionalized Uronic Acids and Sugar Amino Acids

Direct oxidation of the 4,6-O-benzylidene acetal protecting group to C-6 carboxylic acid has been developed that provides an easy access to a wide range of biologically important and synthetically challenging uronic acid and sugar amino acid derivatives in good yields. The RuCl3-NaIO4-mediated oxidative cleavage method eliminates protection and deprotection steps and the reaction takes place under mild conditions. The dual role of the benzylidene acetal, as a protecting group and source of carboxylic acid, was exploited in the efficient synthesis of six-carbon sialic acid analogues and disaccharides bearing uronic acids, including glycosaminoglycan analogues.