113214-71-4

Basic information

• Product Name: b-D-Glucopyranoside, ethyl 1-thio-, 2,3,4,6-tetrabenzoate
• Synonyms: b-D-Glucopyranoside, ethyl 1-thio-, 2,3,4,6-tetrabenzoate;Ethyl 2,3,4,6-tetra-O-benzoyl-1-thio-b-D-glucopyranoside;(2R,3R,4S,5R,6S)-2-((Benzoyloxy)methyl)-6-(ethylthio)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate
• CAS NO: 113214-71-4
• Molecular Formula: C₃₆H₃₂O₉S
• Molecular Weight: 640.69888
• Mol File: 113214-71-4.mol
• Article Data: 15

Chemical Properties

• Appearance: /
• CAS DataBase Reference: b-D-Glucopyranoside, ethyl 1-thio-, 2,3,4,6-tetrabenzoate(CAS DataBase Reference)
• NIST Chemistry Reference: b-D-Glucopyranoside, ethyl 1-thio-, 2,3,4,6-tetrabenzoate(113214-71-4)
• EPA Substance Registry System: b-D-Glucopyranoside, ethyl 1-thio-, 2,3,4,6-tetrabenzoate(113214-71-4)

Safety Data

• Hazardous Substances Data: 113214-71-4(Hazardous Substances Data)

Usage

Uses

(2R,3R,4S,5R,6S)-2-((Benzoyloxy)methyl)-6-(ethylthio)tetrahydro-2H-pyran-3,4,5-triyl Tribenzoate is used as a reactant in the synthesis of oligosaccharides.

Upstream product

• 925-90-6 ethylmagnesium bromide 
• 158419-88-6 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl thiocyanate 
• 98-88-4 benzoyl chloride 
• 7473-36-1 ethyl 1-thio-β-D-glucopyranoside 
• 39483-51-7 ethyl 2,3,4-tri-O-benzyl-1-thio-β-D-glucopyranoside 
• 428816-48-2 2,3,4,6-tetra-O-benzoyl-α-D-glucopyranosyl p-trifluoromethylbenzylthio-p-trifluoromethylphenyl formimidate 
• 2592-58-7 1,2,3,4,6-penta-O-benzoyl-D-glucopyranoside 
• 75-03-6 ethyl iodide 
• 14218-11-2 2,3,4,6-tetra-O-benzoylglucosyl bromide 
• 686299-00-3 ethyl 1-thio-α/β-D-glucopyranoside 
• 158419-90-0 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl thiocyanate 
• 56245-60-4 ethyl 1-thio-β-D-galactopyranoside 
• 55722-49-1 ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside 
• 4163-60-4 β-D-galactose peracetate 

Downstream Products

• 91318-11-5 methyl (2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-(1->6)-2,3,4-tri-O-benzoyl-α-D-glucopyranoside 
• 131643-23-7 C₅₅H₅₂O₁₄ 
• 127588-75-4 C₄₈H₅₀O₁₆ 
• 144102-38-5 C₅₃H₅₆O₁₈ 
• 127588-82-3 3-(benzyloxycarbonylamino)propyl 2,3:6,7-di-O-isopropylidene-4-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-L-glycero-α-D-manno-heptopyranoside 
• 50820-75-2 1-O-acetyl-2,3,4,6-tetra-O-benzoyl-β-D-galactopyranose 
• 2592-58-7 1,2,3,4,6-penta-O-benzoyl-β-D-galactopyranose 
• 131643-22-6 C₄₃H₄₀O₁₄ 
• 166045-47-2 methyl 6-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-β-D-galactopyranoside 
• 166045-52-9 methyl 6-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-α-D-galactopyranoside 
• 171503-77-8 dicyclohexylmethyl 2,3,4-tri-O-benzoyl-6-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-1-thio-β-D-glucopyranoside 
• 159339-64-7 11-hydroxy-3,6,9-trioxaundecanyl 2',3',4',6'-tetra-O-benzoyl-β-D-galactopyranoside 
• 159339-62-5 3-hydroxypropyl 2',3',4',6'-tetra-O-benzoyl-β-D-galactopyranoside 
• 159339-63-6 5-hydroxy-3-oxapentyl 2',3',4',6'-tetra-O-benzoyl-β-D-galactopyranoside 

Relevant articles and documents

Chemical glucosylation of pyridoxine

The chemical synthesis of pyridoxine-5′-β-D-glucoside (5′-β-PNG) was investigated using various glucoside donors and promoters. Hereby, the combination of α4,3-O-isopropylidene pyridoxine, glucose vested with different leaving and protecting groups and the application of stoichiometric amounts of different promoters was examined with regards to the preparation of the twofold protected PNG. Best results were obtained with 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl fluoride and boron trifluoride etherate (2.0 eq.) as promoter at 0 °C (59%). The deprotection was accomplished stepwise with potassium/sodium hydroxide in acetonitrile/water followed by acid hydrolysis with formic acid resulting in the chemical synthesis of 5′-β-PNG.

Urea–hydrogen peroxide prompted the selective and controlled oxidation of thioglycosides into sulfoxides and sulfones

A practical method for the selective and controlled oxidation of thioglycosides to corresponding glycosyl sulfoxides and sulfones is reported using urea–hydrogen peroxide (UHP). A wide range of glycosyl sulfoxides are selectively achieved using 1.5 equiv of UHP at 60 °C while corresponding sulfones are achieved using 2.5 equiv of UHP at 80 °C in acetic acid. Remarkably, oxidation susceptible olefin functional groups were found to be stable during the oxidation of sulfide.

Benzoylated ethyl 1-thioglycosides: Direct preparation from per-O-benzoylated sugars

d-Glucose, lactose, maltose, and melibiose were benzoylated with Bz 2O-Et3N reagent to give fully benzoylated β products. Under the same conditions, d-mannose produced a mixture where the β-benzoate predominated. Treatment of the foregoing compounds with EtSH at slightly elevated temperature (50-60 °C) in the presence of BF 3·Et2O as a promoter gave the corresponding ethyl 1-thio glycosides in high yields. The α-products predominated in all cases in the anomeric mixtures formed. Individual products of all reactions were isolated by chromatography, they were obtained in analytically pure state, and were fully characterized by 1H and 13C NMR data and physical constants.