131531-76-5

Basic information

• Product Name: p-methylphenyl 2,3,4,6-tetra-O-benzyl-thio-β-D-glucopyranoside
• Synonyms: p-methylphenyl 2,3,4,6-tetra-O-benzyl-thio-β-D-glucopyranoside
• CAS NO: 131531-76-5
• Molecular Weight: 646.847
• Mol File: 131531-76-5.mol
• Article Data: 23

Chemical Properties

• CAS DataBase Reference: p-methylphenyl 2,3,4,6-tetra-O-benzyl-thio-β-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: p-methylphenyl 2,3,4,6-tetra-O-benzyl-thio-β-D-glucopyranoside(131531-76-5)
• EPA Substance Registry System: p-methylphenyl 2,3,4,6-tetra-O-benzyl-thio-β-D-glucopyranoside(131531-76-5)

Safety Data

• Hazardous Substances Data: 131531-76-5(Hazardous Substances Data)

Upstream product

• 85982-88-3 1-O-trimethylsilyl-2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside 
• 106-45-6 para-thiocresol 
• 178681-00-0 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl trichloroacetate 
• 28244-94-2 4-methylphenyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside 
• 1152-39-2 p-methylphenyl-1-thio-β-D-galactopyranoside 
• 100-39-0 benzyl bromide 
• 103-19-5 di(p-tolyl) disulfide 
• 100-44-7 benzyl chloride 
• 28244-94-2 p-tolyl-2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 850416-39-6 p-methylphenyl 2,3-di-O-benzyl-4,6-O-(R)-benzylidene-1-thio-β-D-glucopyranoside 
• 219518-19-1 4-methylphenyl 4,6-O-benzylidene-1-thio-β-D-glucopyranoside 
• 1152-39-2 p-methylphenyl 1-thio-β-D-glucopyranoside 
• 596087-18-2 4-methylphenyl 2,3-di-O-benzyl-1-thio-β-D-glucopyranoside 

Downstream Products

• 19488-61-0 methyl 2,3,4,6-tetra-O-benzyl α-D-glucopyranoside 
• 3879-79-6 methyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside 
• 55094-26-3 methyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl-(1-6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 56632-57-6 methyl O-2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->6)-2,3,4-tri-O-benzyll-α-D-glucopyranoside 
• 220645-28-3 p-methylphenyl 2-O-benzoyl-3-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-6-O-tert-butyldiphenylsilyl-4-O-levulinyl-1-thio-β-D-galactopyranoside 
• 55094-26-3 methyl 2,3,4-tri-O-benzyl-6-O-(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl)-α-D-glucopyranoside 
• 55094-26-3 methyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl-(1→6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 6564-72-3 2,3,4,6-tetra-O-benzyl-D-glucopyranose 

Relevant articles and documents

Selective activation of glycosyl donors utilising electrochemical techniques: A study of the thermodynamic oxidation potentials of a range of chalcoglycosides

A series of six chalcoglycosides (phenyl-2,3,4,6-tetra-0-benzoyl-1-seleno-β-D-glucopyranoside, phenyl-2,3,4,6-tetraO-benzyl-1-seleno-β-D-glucopyranoside, phenyl-2,3,4,6-tetra-O-benzyl-1-thio-β-D-glucopyranoside, p-tolyl-2,3,4,6-O-benzoyl-1-thio-β-D-glucop

Synthesis method of voglibose

The invention provides a synthesis method of voglibose, and solves the technical problems that in an existing synthesis method of voglibose, raw materials are difficult to obtain, high in price, large in investment, low in yield and not suitable for industrial production. The synthesis method comprises the steps: synthesizing a compound V by taking glucose monohydrate and sodium acetate as raw materials through eleven reaction steps; and preparing a compound VIII from the compound V through an addition reaction, a ring-opening reaction and an aldol condensation reaction, and thus obtaining voglibose through amination reduction of the compound VIII. The synthesis method of voglibose can be widely applied to the technical field of voglibose synthesis methods.

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.