34361-44-9

Basic information

• Product Name: phenyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1→4)-2,3,6-tri-O-acetyl-α-D-glucopyranoside
• Synonyms: phenyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1→4)-2,3,6-tri-O-acetyl-α-D-glucopyranoside
• CAS NO: 34361-44-9
• Molecular Weight: 712.659
• Mol File: 34361-44-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: phenyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1→4)-2,3,6-tri-O-acetyl-α-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: phenyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1→4)-2,3,6-tri-O-acetyl-α-D-glucopyranoside(34361-44-9)
• EPA Substance Registry System: phenyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1→4)-2,3,6-tri-O-acetyl-α-D-glucopyranoside(34361-44-9)

Safety Data

• Hazardous Substances Data: 34361-44-9(Hazardous Substances Data)

Upstream product

• 3616-19-1 1',2',3',6',2,3,4,6-octa-O-acetyl-β-D-lactose 
• 108-95-2 phenol 
• 5965-66-2 LACTOSE 

Downstream Products

• 847237-52-9 phenyl 2,3,6-tri-O-benzoyl-4-O-(2,3,6-tri-O-benzoyl-β-D-galactopyranosyl)-β-D-glucopyranoside 
• 847237-43-8 C₆₀H₄₉BrO₁₆ 
• 847237-44-9 C₆₀H₅₀O₁₆ 
• 847237-53-0 C₆₀H₅₀O₁₆ 
• 847237-48-3 phenyl 2,3,6-tri-O-benzoyl-4-O-(2,6-di-O-benzoyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-β-D-glucopyranoside 
• 847237-49-4 phenyl 2,3,6-tri-O-benzoyl-4-O-(2,6-di-O-benzoyl-β-D-galactopyranosyl)-β-D-glucopyranoside 
• 847237-50-7 C₅₃H₄₆O₁₅ 
• 847237-65-4 phenyl 4-O-(3-O-allyl-β-D-galactopyranosyl)-β-D-glucopyranoside 
• 847237-47-2 (2S,3R,4R,5S,6R)-5-((3aS,4R,6S,7R,7aR)-7-Hydroxy-4-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-6-hydroxymethyl-2-phenoxy-tetrahydro-pyran-3,4-diol 
• 847237-46-1 phenyl 4-O-(6-deoxy-β-D-galactopyranosyl)-β-D-glucopyranoside 
• 100678-97-5 phenyl (β-D-galactopyranosyl)-(1->4)-β-D-glucopyranoside 
• 34395-01-2 O-β-D-galactopyranosyl-(1<*>4)-1,6-anhydro-β-D-glucopyranoside 

Relevant articles and documents

Trypanosoma cruzi trans-sialidase alternative substrates: Study of the effect of substitution in C-6 in benzyl β-lactoside

Trypanosoma cruzi trans-sialidase (TcTS) is a cell surface protein that participates in the adhesion and invasion mechanisms of the parasite into the host cells, making it an attractive target for inhibitors design. In order to contribute to the knowledge of the interaction between TcTS and their acceptor substrates, we designed and synthesized a library of 20 benzyl lactosides substituted in C-6 of the glucose residue with a series of 1,2,3-triazole derivatives containing different aromatic substituents in the C-4 position. The library was prepared by alkyne-azide cycloaddition reaction catalyzed by Cu(I) (“click chemistry”) between a benzyl β-lactoside functionalized with an azide group in the C-6 position and a series of 2-propargyl phenyl ethers. Herein we analyzed the chromatographic behavior on high performance anion exchange chromatography (HPAEC) of the triazoyl-lactose derivatives and their activity as acceptors of TcTS and inhibitors of the sialylation of N-acetyllactosamine. The triazoyl derivatives were obtained with excellent yields and all of them behaved as moderate alternative substrates. The presence of bulky hydrophobic substituents dramatically increased the retention times in HPAEC but did not affect significantly their acceptor properties toward TcTS.

Synthesis and characterization of 6-O-β-lactosyl-α,β-lactoses, 1-O-(6-O-β-lactosyl-β-lactosyl)-(R,S)-glycerols, and 4,6-di-O-β-D-galactopyranosyl-α,β-D-glucoses

1,2,3,2',3',4',6'-Hepta-O-acetyl-β-lactose (4) was coupled with 2,3,6,2',3',4',6'-hepta-O-acetyl-α-lactosyl bromide (7) in the presence of Hg(CN)2 to afford 1,2,3,2',3',4',6'-hepta-O-acetyl-6-O-(2,3,6,2',3',4',6'-hepta-O- acetyl-β-lactosyl)-β-lactose (11) which, upon O-deacetylation, gave 6-O-β-lactosyl-α,β-lactoses (64% from 4). In contrast, the reaction of 7 with benzyl 2,3,2',3',4',6'-hexa-O-acetyl-β-lactoside in the presence of Hg(CN)2 produced 3,6,2',3',4',6'-hexa-O-acetyl-1,2-O-(2,3,2',3',4',6'-hexa-O-acetyl-1- O-benzyl-β-lactos-6-yl orthoacetyl)-α-lactose (63%) and 3,6,2',3',4',6'-hexa-O-acetyl-1,2-O-(1-cyanoethylidene)-α-lactose (27%). The glycosidation of 4 using 2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl bromide in the presence of Hg(CN)2 afforded, after deprotection, 4,6-di-O-β-D-galactopyranosyl-α,β-D-glucoses (66%). The reaction of 11 with 1,2-di-O-benzyl-(R,S)-glycerols and trimethylsilyl trifluoromethanesulfonate yielded, after deprotection, 1-O-(6-O-β-lactosyl-β-lactosyl)-(R,S)-glycerols (18%). Under the same coupling conditions 11 reacted with 2-O-benzylglycerol to form 3-O-acetyl-2-O-benzyl-1-O-{2',3',4',6'-hexa-O-acetyl-6-O-(2,3,6,2',3' ,4',6'-hepta-O-acetyl-β-lactosyl)-β-lactosyl}-(R,S)-glycerols (16%). 1,2,3,2′,3′,4′,6′-Hepta-O-acetyl-β-lactose (4) was coupled with 2,3,6,2′,3′,4′,6′-hepta-O-Acetyl-α- lactosyl bromide (7) in the presence of Hg(CN)2 to afford 1,2,3,2′,3′,4′,6′-hepta-O-acetyl-6-O-(2,3,6,2′,3$ PRM, 4′,6′-hepta-O-acetyl-6-O-(2,3,6,2′,3′, 4′,-hepta-O-acetyl-β-lactosyl)-β-lactose (11) which, upon O-deacetylation, gave 6-O-β-lactosyl-α,β-lactoses (64% from 4). In contrast, the reaction of 7 with benzyl 2,3,2′,3′,4′,6′-hexa-O-acetyl-β-lactoside in the presence of Hg(CN)2 produced 3,6,2′,3′,4′,6′-hexa-O- acetyl-1,2-O-(2,3,2′,3′,4′,6′-hexa-O-acetyl-1-O-benzy l- β-lactos-6-yl orthoacctyl)-α-lactose (63%) and 3,6,2′,3′,4′,6′-hexa- O-acetyl-1,2-O-(1-cyanoethylidene)-α-lactose (27%). The glycosidation of 4 using 2,3,4,6-tetra-O-acetyl-α-D- galactoyranosyl bromide in the presence of Hg(CN)2 afforded, after deprotection, 4,6-di-O-β-D- galactopyranosyl-α,β-D-glucoses (66%). The reaction of 11 with 1,2-di-O-benzyl-(R,S)-glycerols and trimethylsilyl trifluoromethanesulfonate yielded, after deprotection, 1-O-(6-O-β-lactosyl-β-lactosyl)-(R,S)-glycerols (18%). Under the same coupling conditions II reacted with 2-O-benzylglycerol to form 3-O-acetyl-2-O-benzyl- O-{2′,3′,4′,6′-hexa-O-acetyl-6-O-(2,3,6,2′,3 ′, 4′,6′-hepta-O-acetyl-β-lactosyl)-β-lactosyl}-( R,S)- glycerols (16%).