88087-56-3

Upstream product

• 98-88-4 benzoyl chloride 
• 3396-99-4 methyl α-D-galactopyranoside 
• 53685-07-7 Methyl 3,4-O-isopropylidene-6-O-triphenylmethyl-α-D-galactopyranoside 
• 72659-77-9 methyl 3-O-benzoyl-4,6-O-benzylidene-α-D-galactopyranoside 
• 40269-01-0 methyl 3,4-O-isopropylidene-α-D-galactopyranoside 
• 53685-06-6 methyl 4,6-O-isopropylidene-α-D-galactopyranoside 
• 617-04-9 (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol 
• 1824-94-8 methyl beta-D-galactopyranoside 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 93636-42-1 methyl 2-O-benzoyl-4,6-O-isopropylidene-α-D-galactopyranoside 
• 100221-38-3 Benzoic acid (3aS,4R,6S,7R,7aS)-6-methoxy-2,2-dimethyl-4-trityloxymethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl ester 
• 72659-78-0 methyl 2-O-benzoyl-4,6-O-benzylidene-α-D-galactopyranoside 

Downstream Products

• 401593-04-2 methyl 2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1->3)-2-O-benzoyl-6-O-tert-butyldiphenylsilyl-α-D-galactopyranoside 
• 401593-05-3 methyl 2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1->3)-2-O-benzoyl-α-D-galactopyranoside 
• 401593-03-1 methyl 2-O-benzoyl-6-O-[(tert-butyl)diphenylsilyl]-α-D-galactopyranoside 

Relevant academic research and scientific papers

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.

Magnesium ion enhances lanthanum-promoted monobenzoylation of a monosaccharide in water

Magnesium ion combines selectively with the methyl phosphate by-product in the lanthanum-promoted biomimetic reaction of benzoyl methyl phosphate with monosaccharides.

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

Synthesis of a hexasaccharide that relates to the arabinogalactan epitope

A hexasaccharide derivative of the arabinogalactan epitope, methyl β-D-galactopyranosyl-(1 → 6)-[α-L-arabinofuranosyl-(1 → 3)]-β-D-galactopyranosyl-(1 → 6)-β-D-galactopyranosyl-(1 → 6)-[α-L-arabinofuranosyl-(1 → 3)]-α-D-galactopyranoside, was synthesized efficiently using a 3 + 3 strategy. The key step is the preparation of the trisaccharide donor, isopropyl 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl-(1 → 6)-[2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1 → 3)]-2,4-di-O-benzoyl-1-thio-β-D-galactopyranoside, from isopropyl 1-thio-β-D-galactopyranoside using a one-pot synthesis of a 3,6-differentially protected building block.

Tin-mediated regioselective acylation of unprotected sugars on solid phase

Methyl α-D-glucopyranoside, methyl α-D-mannopyranoside and methyl β-D-galactopyranoside bound on O-6 to a copolystyrene-DVB resin through a trityl ether linker, have been regioselectively acylated with benzoyl chloride after treatment with Bu2S

2-Substituted methyl alpha-D-galactopyranosides: synthesis and binding affinity for the A and B subunits of the Griffonia simplicifolia I isolectins.

The binding affinities of the N-acetyl, N-trifluoroacetyl, N-propionyl, N-formyl, N-benzoyl, N-p-nitrobenzoyl, N-p-aminobenzoyl, and N-methyl derivatives of methyl 2-amino-2-deoxy-alpha-D-galactopyranoside and the 2-O-acetyl, -benzoyl, -benzyl, and -methyl derivatives of methyl alpha-D-galactopyranoside for the A and B subunits of the Griffonia simplicifolia I isolectins have been determined by hapten inhibition analysis of a galactomannan-isolectin precipitation system. Models for these carbohydrate-protein interactions are presented together with an interpretation of the results on the basis of electronic and steric effects.

Regioselective Monoacylation of Some Glycopyranosides via Cyclic Tin Intermediates

Selective mono-benzoylation of some pento- and hexo-pyranosides (Me β-L-Ara, Ph α-L-Ara, Me α-D-Xyl, Me β-D-Xyl, Me α-D-Glc, Me-β-D-Glc, Me α-D-Gal, Me β-D-Gal, and Me α-D-Man) by using Bu2SnO was examined in comparaison with the results of the (Bu3Sn)2O method and direct benzoylation.The Bu2SnO method is particularly useful in that it selectively activates an equatorial hydroxyl group wich bears an oxygenated function (OH or OMe) in a cis relationship at an adjacent position, even in the presence of a more reactive primary OH group.The various mono- and di-O-benzoyl derivatives prepared in this work were unambiguously identified by analysis of their 13C-nuclear magnetic resonance spectra.