211678-08-9

Basic information

• Product Name: p-methylphenyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranoside
• Synonyms: p-methylphenyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranoside
• CAS NO: 211678-08-9
• Molecular Weight: 646.847
• Mol File: 211678-08-9.mol
• Article Data: 17

Chemical Properties

• CAS DataBase Reference: p-methylphenyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: p-methylphenyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranoside(211678-08-9)
• EPA Substance Registry System: p-methylphenyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranoside(211678-08-9)

Safety Data

• Hazardous Substances Data: 211678-08-9(Hazardous Substances Data)

Upstream product

• 25878-60-8 D-galactose pentaacetate 
• 106-45-6 para-thiocresol 
• 28244-94-2 4-methylphenyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside 
• 100-39-0 benzyl bromide 
• 1152-39-2 p-methylphenyl-1-thio-β-D-galactopyranoside 
• 6386-24-9 2,3,4,6-tetra-O-benzyl-D-galactopyranose 
• 211801-73-9 C₇₇H₉₀O₅SSi₄ 
• 4163-60-4 β-D-galactose peracetate 

Downstream Products

• 1206803-27-1 p-methylphenyl 2,3,4-tri-O-benzyl-6-O-triethyl-silyl-1-thio-β-D-galactopyranoside 
• 1407151-84-1 p-tolyl 6-O-(2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-2,3,4-tri-O-benzylthio-β-D-galactopyranoside 
• 1143374-19-9 C₅₄H₅₅N₃O₉S 
• 1427297-45-7 p-tolyl 2,3,4,6-tetra-O-benzyl-D-galactopyranosyl-α(1→3)-4,6-O-benzylidene-2-O-benzyl-thio-β-D-galactopyranoside 
• 1427297-46-8 methyl 2,3,4,6-tetra-O-benzyl-D-galactopyranosyl-α(1→3)-4,6-O-benzylidene-2-O-benzyl-D-galactopyranosyl-α(1→4)-2,3-O-isopropylidene-α-L-rhamnopyranoside 
• 1427297-38-8 p-tolyl 2,3,4,6-tetra-O-benzyl-D-galactopyranosyl-α(1→3)-2,4,6-tri-O-benzyl-thio-β-D-glucopyranoside 
• 3879-79-6 methyl 2,3,4,6-tetra-O-benzyl α-D-galactopyranoside 
• 53008-63-2 methyl 2,3,4,6-tetra-O-benzyl-α-D-galactopyranoside 
• 918161-01-0 p-methylphenyl 2,3-di-O-benzoyl-6-O-benzyl-4-O-(2',3',4',6'-tetra-O-benzyl-α-D-galactopyranosyl)-1-thio-β-D-galactopyranoside 

Relevant articles and documents

Automated Quantification of Hydroxyl Reactivities: Prediction of Glycosylation Reactions

The stereoselectivity and yield in glycosylation reactions are paramount but unpredictable. We have developed a database of acceptor nucleophilic constants (Aka) to quantify the nucleophilicity of hydroxyl groups in glycosylation influenced by the steric, electronic and structural effects, providing a connection between experiments and computer algorithms. The subtle reactivity differences among the hydroxyl groups on various carbohydrate molecules can be defined by Aka, which is easily accessible by a simple and convenient automation system to assure high reproducibility and accuracy. A diverse range of glycosylation donors and acceptors with well-defined reactivity and promoters were organized and processed by the designed software program “GlycoComputer” for prediction of glycosylation reactions without involving sophisticated computational processing. The importance of Aka was further verified by random forest algorithm, and the applicability was tested by the synthesis of a Lewis A skeleton to show that the stereoselectivity and yield can be accurately estimated.

Establishment of Guidelines for the Control of Glycosylation Reactions and Intermediates by Quantitative Assessment of Reactivity

Stereocontrolled chemical glycosylation remains a major challenge despite vast efforts reported over many decades and so far still mainly relies on trial and error. Now it is shown that the relative reactivity value (RRV) of thioglycosides is an indicator for revealing stereoselectivities according to four types of acceptors. Mechanistic studies show that the reaction is dominated by two distinct intermediates: glycosyl triflates and glycosyl halides from N-halosuccinimide (NXS)/TfOH. The formation of glycosyl halide is highly correlated with the production of α-glycoside. These findings enable glycosylation reactions to be foreseen by using RRVs as an α/β-selectivity indicator and guidelines and rules to be developed for stereocontrolled glycosylation.

COMPOSITIONS AND METHODS FOR THE TREATMENT OF BACTERIAL INFECTIONS

Compositions and methods for the treatment of bacterial infections include compounds containing dimers of cyclic heptapeptides conjugated to one or more monosaccharide or oligosaccharide moieties. In particular, compounds can be used in the treatment of bacterial infections caused by Gram-negative bacteria.