88087-59-6

Basic information

• Product Name: methyl 6-O-benzoyl-α-D-mannopyranoside
• Synonyms: methyl 6-O-benzoyl-α-D-mannopyranoside
• CAS NO: 88087-59-6
• Molecular Weight: 298.293
• Mol File: 88087-59-6.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: methyl 6-O-benzoyl-α-D-mannopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 6-O-benzoyl-α-D-mannopyranoside(88087-59-6)
• EPA Substance Registry System: methyl 6-O-benzoyl-α-D-mannopyranoside(88087-59-6)

Safety Data

• Hazardous Substances Data: 88087-59-6(Hazardous Substances Data)

Upstream product

• 98-88-4 benzoyl chloride 
• 617-04-9 (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 3396-99-4 methyl α-D-galactopyranoside 
• 613-90-1 benzoyl cyanide 
• 91685-05-1 methyl 3-O-benzoyl-4, 6-O-benzylidene-α-D-mannopyranoside 
• 65-85-0 benzoic acid 
• 1523-15-5 2,4-dinitrophenyl benzoate 

Downstream Products

• 51996-10-2 methyl 2-O-acetyl-3,4,6-tri-O-benzoyl-α-D-mannopyranoside 
• 80245-08-5 methyl 3,4,6-tri-O-benzoyl-α-D-mannopyranoside 
• 225917-95-3 Benzoic acid (2R,3R,4S,5S,6S)-3,5-dihydroxy-6-methoxy-4-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester 

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.

Chiral copper(II) complex-catalyzed reactions of partially protected carbohydrates

Catalyst-controlled regioselective functionalization of partially protected saccharide molecules is a highly important yet under-developed area of carbohydrate chemistry. Such reactions allow for the reduction of protecting group manipulation steps required in syntheses involving sugars. Herein, an approach to these processes using enantiopure copper-bis(oxazoline) catalysts to control couplings of electrophiles to various partially protected sugars is reported. In a number of cases, divergent regioselectivity was observed as a function of the enantiomer of catalyst that is used.

Lanthanum-catalyzed aqueous acylation of monosaccharides by benzoyl methyl phosphate

It was previously reported that diols dissolved in water (pH 8, EPPS buffer) react with benzoyl methyl phosphate (BMP) in the presence of lanthanide ions to form monobenzoyl esters. We have investigated the possibility of extending this process to include