4338-28-7

Basic information

• Product Name: (6-O-benzoyl)-methyl-α-D-glucopyranoside
• Synonyms: (6-O-benzoyl)-methyl-α-D-glucopyranoside
• CAS NO: 4338-28-7
• Molecular Weight: 298.293
• Mol File: 4338-28-7.mol
• Article Data: 16

Chemical Properties

• CAS DataBase Reference: (6-O-benzoyl)-methyl-α-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: (6-O-benzoyl)-methyl-α-D-glucopyranoside(4338-28-7)
• EPA Substance Registry System: (6-O-benzoyl)-methyl-α-D-glucopyranoside(4338-28-7)

Safety Data

• Hazardous Substances Data: 4338-28-7(Hazardous Substances Data)

Upstream product

• 97-30-3 methyl-alpha-D-glucopyranoside 
• 10364-94-0 1-benzoylimidazole 
• 769-78-8 vinyl benzoate 
• 93-97-0 benzoic acid anhydride 
• 3162-96-7 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside 
• 65-85-0 benzoic acid 
• 98-88-4 benzoyl chloride 
• 32849-03-9 methyl 2,3,4,6-tetra-O-benzoyl-α-D-glycopyranoside 
• 1523-15-5 2,4-dinitrophenyl benzoate 

Downstream Products

• 1451062-76-2 (6-O-benzoyl)-methyl-α-D-ribo-hexapyranoside-3-ulose 
• 32849-04-0 methyl 2,3,4-tri-O-acetyl-6-O-benzoyl-α-D-glucopyranoside 
• 1340482-37-2 methyl 2-O-(2',3',4',6'-tetra-O-benzyl-α-D-glucopyranosyl)-α-D-glucopyranoside 
• 1340482-38-3 methyl 2-O-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl)-α-D-glucopyranoside 
• 1340482-39-4 methyl 3-O-(2',3',4',6'-tetra-O-benzyl-α-D-glucopyranosyl)-α-D-glucopyranoside 
• 1340482-40-7 methyl 3-O-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl)-α-D-glucopyranoside 

Relevant articles and documents

Lead-Catalyzed Aqueous Benzoylation of Carbohydrates with an Acyl Phosphate Ester

Biochemical systems utilize adenylates of amino acids to aminoacylate the 3′-terminal diols of tRNAs. The reactive acyl group of the biological acylation agent is a subset of the general class of acyl phosphate monoesters. Those compounds are relatively stable in aqueous solutions, and their alkyl esters are conveniently prepared. It has previously been shown that biomimetic reactions of acyl phosphate monoesters with diols and carbohydrates are promoted by lanthanide salts. However, they also promote hydrolysis of acyl phosphate reagents, and the overall yields are modest. An assessment of the catalytic potential of alternative Lewis acids reveals that lead ions may be more effective as catalysts than lanthanides. Treatment of carbohydrates with benzoyl methyl phosphate (BMP) and triethylamine in water with added lead nitrate produces monobenzoyl esters in up to 75% yield. This provides a water-compatible pathway for novel patterns of benzoylation of polyhydroxylic compounds.

Donor specificity and regioselectivity in Lipolase mediated acylations of methyl α-d-glucopyranoside by vinyl esters of phenolic acids and their analogues

Methyl α-d-glucopyranoside as a model acceptor was acylated by several phenolic and non-phenolic vinyl esters using immobilised Lipolase. Donor specificity and regioselectivity of reaction were investigated. Conversion and rate of acylation by structurally varied donors indicates that the synthetic reactivity of Lipolase corresponds to the hydrolytic activity of feruloyl esterase type A. Lipolase exhibited remarkable regioselectivity for primary position of methyl α-d-glucopyranoside. The acylation occurred exclusively at 6-O primary position when vinyl esters of phenolic acids (hydroxybenzoates, hydroxyphenylalkanoates and hydroxycinnamates) served as acyl donors (5-77%). In addition to the major 6-O-acyl products (52-79%), 2,6-di-O-acylated derivatives were isolated from reaction mixtures (2-13%) when non-phenolic donors were used (vinyl esters of fully methoxylated derivatives of phenolic acids, along with vinyl benzoates, cinnamates or some heterocyclic analogues).

Efficient and controllably selective preparation of esters using uronium-based coupling agents

Carboxylic acid esters can be prepared in excellent yields at room temperature from an acid and either a phenol or an aliphatic alcohol using the peptide coupling reagents, TBTU, TATU, or COMU, in the presence of organic bases. Reactions using TBTU and TATU are faster but do not occur with tertiary alcohols. Selectivity between reaction with primary or secondary alcohols in diols and polyols can be achieved with choice of base and coupling agent.