850416-39-6

Basic information

• Product Name: 4-Methylphenyl2,3-bis-O-(phenylmethyl)-4,6-O-[(R)-phenylmethylene]-1-thio-β-D-Glucopyranoside
• Synonyms: 4-Methylphenyl2,3-bis-O-(phenylmethyl)-4,6-O-[(R)-phenylmethylene]-1-thio-β-D-Glucopyranoside; 4-METHYLPHENYL 2,3-BIS-O-(PHENYLMETHYL)-4,6-O-[(R)-PHENYLMETHYLENE]-1-THIO-B-D-GLUCOPYRANOSIDE
• CAS NO: 850416-39-6
• Molecular Formula: C₃₄H₃₄O₅S
• Molecular Weight: 554.704
• Mol File: 850416-39-6.mol
• Article Data: 11

Chemical Properties

• Melting Point: 123-125 °C
• Boiling Point: 682.4±55.0 °C(Predicted)
• Appearance: /
• Density: 1.25±0.1 g/cm3(Predicted)
• CAS DataBase Reference: 4-Methylphenyl2,3-bis-O-(phenylmethyl)-4,6-O-[(R)-phenylmethylene]-1-thio-β-D-Glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Methylphenyl2,3-bis-O-(phenylmethyl)-4,6-O-[(R)-phenylmethylene]-1-thio-β-D-Glucopyranoside(850416-39-6)
• EPA Substance Registry System: 4-Methylphenyl2,3-bis-O-(phenylmethyl)-4,6-O-[(R)-phenylmethylene]-1-thio-β-D-Glucopyranoside(850416-39-6)

Safety Data

• Hazardous Substances Data: 850416-39-6(Hazardous Substances Data)

Usage

General Description

4-Methylphenyl2,3-bis-O-(phenylmethyl)-4,6-O-[(R)-phenylmethylene]-1-thio-β-D-Glucopyranoside is a complex chemical compound. It is a glucoside, which means it is a type of sugar molecule that is linked to a non-sugar molecule. The chemical structure of this compound includes a glucose molecule with a thioether linkage, as well as multiple phenylmethyl and phenylmethylene groups attached to the glucose molecule at various positions. 4-Methylphenyl2,3-bis-O-(phenylmethyl)-4,6-O-[(R)-phenylmethylene]-1-thio-β-D-Glucopyranoside is likely to have specialized applications in fields such as organic chemistry and biochemistry, where its unique chemical structure may be exploited for specific purposes.

Upstream product

• 100-52-7 benzaldehyde 
• 596087-18-2 4-methylphenyl 2,3-di-O-benzyl-1-thio-β-D-glucopyranoside 
• 868241-49-0 (p-methylphenyl) 4,6-O-benzylidene-1-thio-β-D-glucopyranoside 
• 100-39-0 benzyl bromide 
• 219518-19-1 4-methylphenyl 4,6-O-benzylidene-1-thio-β-D-glucopyranoside 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 1152-39-2 p-methylphenyl 1-thio-β-D-glucopyranoside 
• 604-69-3 β-D-glucose pentaacetate 
• 106-45-6 para-thiocresol 
• 28244-94-2 p-tolyl-2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside 
• 942043-17-6 4-methylphenyl 2,3,4,6-tetrakis-O-trimethylsilyl-1-thio-β-D-glucopyranoside 
• 28244-94-2 4-methylphenyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside 

Downstream Products

• 851895-41-5 p-methylphenyl 2,3,6-tri-O-benzyl-1-deoxy-1-thio-β-D-glucopyranoside 
• 479252-05-6 ((2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-p-tolylsulfanyl-tetrahydro-pyran-2-yl)-methanol 
• 20770-84-7 2,3-di-O-benzyl-4,6-O-benzylidene-D-glucopyranose 
• 596087-18-2 4-methylphenyl 2,3-di-O-benzyl-1-thio-β-D-glucopyranoside 
• 918948-30-8 C₇₄H₇₃N₃O₁₁SSi 
• 596087-20-6 (2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-6-p-tolylsulfanyl-tetrahydro-pyran-3-ol 
• 131531-76-5 p-methylphenyl 2,3,4,6-tetra-O-benzyl-thio-β-D-glucopyranoside 

Relevant articles and documents

Stereoselective Phenylselenoglycosylation of Glycals Bearing a Fused Carbonate Moiety toward the Synthesis of 2-Deoxy-β-galactosides and β-Mannosides

A phenylselenoglycosylation reaction of glycal derivatives mediated by diphenyl diselenide and phenyliodine(III) bis(trifluoroacetate) under mild conditions is described. Stereoselective glycosylation has been achieved by installing fused carbonate on those glycals. 3,4-O-Carbonate galactals and 2,3-O-carbonate 2-hydroxyglucals are converted into corresponding glycosides in good yields with excellent β-selectivity, resulting in 2-phenylseleno-2-deoxy-β-galactosides and 2-phenylseleno-β-mannosides which are good precursors of 2-deoxy-β-galactosides and β-mannosides, respectively.

Simple and Practical Real-Time Analysis of Solid-Phase Reactions by Thin-Layer Chromatography

Solid-phase synthesis is a practical approach for simplifying the time-consuming and routine purification steps in the preparation of numerous naturally occurring molecules; however, studying such reactions is difficult due to the lack of a convenient monitoring method. By using thin-layer chromatography in conjunction with a photolabile linker on a resin, we developed a convenient and simple method for monitoring solid-phase reactions in real time by thin-layer chromatography. This method provides a user-friendly protocol for examining reaction conditions for solid-state syntheses.

TMSBr-mediated solvent- and work-up-free synthesis of α-2-deoxyglycosides from glycals

The thio-additions of glycals were efficiently promoted by a stoichiometric amount of trimethylsilyl bromide (TMSBr) to produce S-2-deoxyglycosides under solvent-free conditions in good to excellent yields. In addition, with triphenylphosphine oxide as an additive, the TMSBr-mediated direct glycosylations of glycals with a large range of alcohols were highly α-selective.