257286-41-2

Upstream product

• 362608-43-3 ethyl 3,4-di-O-isopropylidene-2-O-(p-methoxybenzyl)-6-O-(2-methoxy-2-propyl)-1-thio-β-D-galactopyranoside 
• 56245-60-4 ethyl 1-thio-β-D-galactopyranoside 
• 206857-11-6 ethyl 3,4-O-isopropylidene-6-O-(1-methoxy-1-methylethyl)-1-thio-β-D-galactopyranoside 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 73842-99-6 3-tert-butyldimethylsilyloxy-1-propanol 
• 257286-40-1 1-O-tert-butyldimethylsilyloxy-3-O-methanesulfonyloxy-propane 
• 206857-12-7 ethyl 3,4-O-isopropylidene-2-O-p-methoxybenzyl-1-thio-β-D-galactopyranoside 

Downstream Products

• 257286-47-8 methyl 2-acetamido-6-O-benzyl-2-deoxy-4-O-(3,4-O-isopropylidene-2-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-β-D-galactopyranosyl)-3,6'-di-O-(propan-1,3-diyl)-β-D-glucopyranoside 
• 257286-45-6 ethyl 3,4-O-isopropylidene-2-O-p-methoxybenzyl-6-O-(3'-O-(methyl 2-acetamido-6-O-benzyl-2-deoxy-β-D-glucopyranos-3-oxy)propyl)-1-thio-β-D-galactopyranoside 
• 257286-46-7 methyl 2-acetamido-6-O-benzyl-2-deoxy-4-O-(3,4-O-isopropylidene-2-O-p-methoxybenzyl-β-D-galactopyranosyl)-3,6'-di-O-(propan-1,3-diyl)-β-D-glucopyranoside 
• 257286-39-8 methyl 2-acetamido-6-O-benzyl-2-deoxy-4-O-(3,4-O-isopropylidene-β-D-galactopyranosyl)-3,6'-di-O-(propan-1,3-diyl)-β-D-glucopyranoside 
• 257286-43-4 ethyl 3,4-O-isopropylidene-2-O-p-methoxybenzyl-6-O-(3'-methanesulfonyloxypropyl)-1-thio-β-D-galactopyranoside 
• 257286-42-3 ethyl 3,4-O-isopropylidene-2-O-p-methoxybenzyl-6-O-(3'-hydroxypropyl)-1-thio-β-D-galactopyranoside 

Relevant academic research and scientific papers

Constrained H-Type 2 Blood Group Trisaccharide Synthesized in a Bioactive Conformation via Intramolecular Glycosylation

The methyl glycoside of the H-type 2 trisaccharide 1 was synthesized in a constrained, bioactive conformation via intramolecular aglycon delivery. Computer modeling of the crystal structure of the Ulex europaeus I lectin with a docked H-type 2 trisaccharide suggested that the disaccharide Galp(1→4)GlcpNAcl→OCH3 could be tethered in a bioactive conformation if Gal O-6 and GlcNAc O-3 are linked via a three-carbon tether. The ethyl 1-thiogalactopyranoside 13 was used to alkylate the methyl 2-acetamido-2-deoxy glucopyranoside 7, and the resulting dimer was subjected to intramolecular glycosylation following protecting group manipulation. The tethered disaccharide 4 was glycosylated by the activated fucopyranosyl donor 3 to give the protected target molecule 17. Solid-phase binding assays showed that the tethered trisaccharide 2 was 3-fold less active than native H-type 2 trisaccharide 1 when assayed against the U. europaeus I lectin, whereas it was 250 times less active when assayed with the Psophocarpus tetragonolobus II lectin. The observed activities are consistent with published models for H-trisaccharide interactions with Ulex and Psophocarpus lectins and provide further evidence that suggests reduction of oligosaccharide flexibility by intramolecular tethering provides no significant gain in binding energy.