85951-07-1

Basic information

• Product Name: methyl O³-benzoyl-α-D-mannoside
• Synonyms: methyl O³-benzoyl-α-D-mannoside
• CAS NO: 85951-07-1
• Molecular Weight: 298.293
• Mol File: 85951-07-1.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: methyl O³-benzoyl-α-D-mannoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl O³-benzoyl-α-D-mannoside(85951-07-1)
• EPA Substance Registry System: methyl O³-benzoyl-α-D-mannoside(85951-07-1)

Safety Data

• Hazardous Substances Data: 85951-07-1(Hazardous Substances Data)

Upstream product

• 617-04-9 (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol 
• 91685-05-1 methyl 3-O-benzoyl-4, 6-O-benzylidene-α-D-mannopyranoside 
• 98-88-4 benzoyl chloride 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 3396-99-4 methyl α-D-galactopyranoside 

Downstream Products

• 1073186-58-9 methyl O³-benzoyl-O⁶-p-toluenesulfonyl-α-D-mannoside 

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.

Selectivity switch in the catalytic functionalization of nonprotected carbohydrates: Selective synthesis in the presence of anomeric and structurally similar carbohydrates under mild conditions

A catalytic process for the chemo- and regioselective functionalization of nonprotected carbohydrates has been developed. This novel process allows selective thiocarbonylation, acylation, and sulfonylation of a particular hydroxy group in a particular carbohydrate in the simultaneous presence of structurally similar carbohydrates such as anomers. In addition, the chemoselectivity can be switched by regulating only the length of the alkyl chain in the organotin catalyst.

Chelation-controlled regioselectivity in the lanthanum-promoted monobenzoylation of monosaccharides in water

Monosaccharides are selectively converted to monobenzoates in a base-catalyzed reaction with benzoyl methyl phosphate (BzMP) and a lanthanum salt in water. Yields are reported in terms of formation of the ester, which competes with hydrolysis of BzMP, to