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

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

Used in Pharmaceutical Industry:
b-D-Glucopyranoside, ethyl 1-thio-, 2,3,4,6-tetrabenzoate is used as a reactant for the synthesis of oligosaccharides, which are essential in the development of new drugs and therapies. Oligosaccharides play a crucial role in various biological processes, including cell signaling, immune response, and molecular recognition. The unique structure of this compound allows for the creation of specific oligosaccharides with tailored properties, making it a valuable asset in the pharmaceutical industry.
Used in Chemical Synthesis:
In the field of chemical synthesis, b-D-Glucopyranoside, ethyl 1-thio-, 2,3,4,6-tetrabenzoate serves as an intermediate or building block for the creation of more complex molecules. Its unique structure and functional groups make it a versatile component in the synthesis of various organic compounds, including those with potential applications in materials science, pharmaceuticals, and other industries.
Used in Research and Development:
Due to its unique structure and potential applications, b-D-Glucopyranoside, ethyl 1-thio-, 2,3,4,6-tetrabenzoate is also used in research and development settings. Scientists and researchers can utilize this compound to study its properties, interactions with other molecules, and potential applications in various fields. This can lead to the discovery of new compounds, materials, or therapeutic approaches based on the unique characteristics of this compound.

Upstream product

• 98-88-4 benzoyl chloride 
• 7473-36-1 ethyl 1-thio-β-D-glucopyranoside 
• 2592-58-7 1,2,3,4,6-penta-O-benzoyl-D-glucopyranoside 
• 75-03-6 ethyl iodide 
• 2280-44-6 D-Glucose 
• 93-97-0 benzoic acid anhydride 
• 75-08-1 ethanethiol 
• 2592-58-7 1,2,3,4,6-penta-O-benzoyl-β-D-glucopyranose 
• 10257-28-0 D-Galactose 
• 2592-58-7 1,2,3,4,6-penta-O-benzoyl-α-D-galactopyranoside 
• 61198-88-7 2,3,4,6-tetra-O-benzoyl-α-D-galactopyranosyl bromide 
• 4163-60-4 β-D-galactose peracetate 
• 55722-49-1 ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside 
• 2592-58-7 1,2,3,4,6-penta-O-benzoyl-β-D-galactopyranose 

Downstream Products

• 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 
• 128503-39-9 methyl 2,3,4-tri-O-benzoyl-6-O-(2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl)-α-D-glucopyranoside 
• 496810-91-4 4-bromophenyl (2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-benzoyl-1-thio-β-D-glucopyranoside 
• 120969-06-4 diosgenyl 2,3,4,6-O-tetra-benzoyl-β-D-glucuronopyranoside 
• 14144-06-0 trillin 
• 60478-68-4 dioscin 

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.

Visible Light Enables Aerobic Iodine Catalyzed Glycosylation

A versatile protocol for light induced catalytic activation of thioglycosides using iodine as an inexpensive and readily available photocatalyst was developed. Oxygen serves as a green and cost-efficient terminal oxidant and irradiation is performed with a common household LED-bulb. The scope of this glycosylation protocol was investigated in the synthesis of O-glycosides with yields up to 95 %.

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.

SYNTHESIS OF AMPHIPHILIC CALIXARENE GLYCOSIDE DETERGENTS AND USE OF SAME FOR EXTRACTING AND STABILIZING NATIVE FUNCTIONAL MEMBRANE PROTEINS

Calixarene compound according to formula (I) wherein: R1 represents a linear or branched C(1-16) alkyl group; R2 represents an hydrogen atom or a methyl group; R3 is identical to R1 or R2 g

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.

Novel approaches for the synthesis and activation of thio- and selenoglycoside donors

(Chemical Equation Presented) Alkyl thio-, phenyl seleno-, and phenyl thioglycosides can be prepared through short synthetic sequences based on the generation of glycosyl iodides as versatile intermediates. In addition, a novel cheap combined system (stoichiometric NBS and catalytic Bi(OTf)3) has been developed for rapid and efficient activation of a wide variety of thio- and selenoglycoside donors.

Acylation of carbohydrates over Al2O3: Preparation of partially and fully acylated carbohydrate derivatives and acetylated glycosyl chlorides

Selective and per-O-acylation of carbohydrate derivatives using acyl chlorides and Al2O3, a solid support reagent, is reported. This protocol does not require the addition of any base or activator. This methodology has been further extended to the selective acylation of carbohydrate diols and the one-pot preparation of acetylated glycosyl chlorides direct from free reducing sugars. The yields obtained in most of the cases are excellent.

SPECIFIC ANTAGONIST FOR BOTH E- AND P-SELECTINS

Compounds and methods are provided for modulating in vitro and in vivo processes mediated by selectin binding. More specifically, selectin modulators and their use are described, wherein the selectin modulators that modulate (e.g., inhibit or enhance) a selectin-mediated function comprise a particular glycomimetic linked to a particular BASA (Benzyl Amino Sulfonic Acid).

Catalytic and stereoselective glycosylation with a novel and efficient disarmed glycosyl donor: Glycosyl p-trifluoromethylbenzylthio-p-trifluoromethylphenyl formimidate

A novel and efficient glycosyl donor having a p-trifluoromethylbenzylthio-p-trifluoromethylphenyl formimidate function as a leaving group is easily prepared by the addition of anomeric hydroxyl group of 2,3,4,6-tetra-O-benzoyl-α,β-D-glucopyranose to p-trifluoromethylphenyl isothiocyanate, followed by treatment with p-trifluoromethylbenzyl bromide. Catalytic and stereoselecrive glycosylation using this glycosyl donor effectively proceeds by activating its nitorogen atom with various protic and Lewis acids.

Scope and applications of "active and latent" thioglycosyl donors. Part 4

The relative reactivity of various thioglycosyl donors having ethyl, phenyl, or parasubstituted phenyl groups with electron donating (N-Ac) or electron withdrawing (NO2) substituents were compared using 1,2:3,4-di-O-isopropylidene-α-D-galactopy