154391-03-4

Upstream product

• 98-88-4 benzoyl chloride 
• 154391-02-3 allyl 2,3-di-O-benzoyl-4,6-O-benzylidene-α-D-galactopyranoside 

Downstream Products

• 154391-06-7 allyl 2,3-di-O-benzoyl-4,6-O-<(R)-1-methoxycarbonylethylidene>-α-D-galactopyranoside 
• 874904-99-1 allyl 2,3-di-O-benzoyl-6-O-(methyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-5-phthalimido-D-glycero-α-D-galacto-2-nonulopyranosylonate)-α-D-galactopyranoside 
• 1179813-93-4 allyl 2,3-di-O-benzoyl-6-O-(methyl-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-5-azido-D-glycero-α-D-galacto-nonulopyranosyloate)-α-D-galactopyranoside 
• 874904-96-8 allyl 2,3-di-O-benzoyl-6-O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-α-D-galactopyranoside 

Relevant academic research and scientific papers

Boronic Acids as Phase-Transfer Reagents for Fischer Glycosidations in Low-Polarity Solvents

Protocols employing phenylboronic acid as a phase-transfer reagent for Fischer glycosidations in low-polarity organic solvents are described. In addition to providing rate acceleration, the formation of a substrate-derived boronic ester alters the course of the reaction by selective promotion of a furanoside- or pyranoside-selective pathway. Computational modeling of the relative energies of the glycoside-derived boronic esters provides results that are qualitatively consistent with the observed distributions of furanoside versus pyranoside products. The boronic esters that are obtained as direct products of these reactions serve as protected intermediates for the synthesis of functionalized glycosides. Complexation of particular diol groups by the boronic acid also enables selective transformations of mixtures of carbohydrates.

Synthesis of 5-aminopentyl 4,6-O--β-D-galactopyranoside and its use as a ligand for the affinity chromatography of human serum amyloid P protein

A series of 2,3-di-O-benzoyl-D-galctopyranosides, α-allyl (5), α-benzyl (6), β-ethyl-1-thio (7), β-phenyl-1-thio (8), and α-methyl (9), were prepared from the corresponding 4,6-O-benzylidene derivatives and were acetalated in acetonitrile with methyl pyruvate, to give diastereoselectively the 2,3-di-O-benzoyl-4,6-O--D-galactopyranosides 10-16.The latter were converted into the 2,3-di-O-benzoyl-4,6-O--D-galactopyranosyl α- and β-trichloroacetimidates 19 and 20, α- and β-fluorides 21 and 22, the α-bromide 23, and the α-chloride 24, respectively.These donors, including the phenyl 1-thiogalactoside 14, reacted with 5-pentanol to give the corresponding protected β-D-galactoside 27, deblocking of which afforded the title compound 1.Binding of 1 to epoxypropyl-modified acrylamide beads gave an affinity adsorbent that was used to isolate serum amyloid P protein from human serum.