38184-10-0

Basic information

• Product Name: .beta.-D-Glucopyranoside, phenyl 2,3,4,6-tetrakis-O-(phenylmethyl)-1-thio-
• Synonyms: .beta.-D-Glucopyranoside, phenyl 2,3,4,6-tetrakis-O-(phenylmethyl)-1-thio-;Phenyl2,3,4,6-tetra-O-benzyl-b-D-thioglucopyranoside;phenyl 2,3,4,6-tetra-O-benzyl-1-deoxy-1-thio-β-D-glucopyranoside;(2R,3R,4S,5R,6S)-3,4,5-Tris(benzyloxy)-2-((benzyloxy)methyl)-6-(phenylthio)tetrahydro-2H-pyran
• CAS NO: 38184-10-0
• Molecular Formula: C₄₀H₄₀O₅S
• Molecular Weight: 632.81
• Mol File: 38184-10-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: .beta.-D-Glucopyranoside, phenyl 2,3,4,6-tetrakis-O-(phenylmethyl)-1-thio-(CAS DataBase Reference)
• NIST Chemistry Reference: .beta.-D-Glucopyranoside, phenyl 2,3,4,6-tetrakis-O-(phenylmethyl)-1-thio-(38184-10-0)
• EPA Substance Registry System: .beta.-D-Glucopyranoside, phenyl 2,3,4,6-tetrakis-O-(phenylmethyl)-1-thio-(38184-10-0)

Safety Data

• Hazardous Substances Data: 38184-10-0(Hazardous Substances Data)

Usage

Uses

Used in Organic Chemistry:
.beta.-D-Glucopyranoside, phenyl 2,3,4,6-tetrakis-O-(phenylmethyl)-1-thiois used as a glycosylating agent for the synthesis of complex carbohydrates and their derivatives. Its application in this field is due to its ability to facilitate the formation of glycosidic bonds, which are crucial for the structure and function of many biologically important molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, .beta.-D-Glucopyranoside, phenyl 2,3,4,6-tetrakis-O-(phenylmethyl)-1-thiois used as a key intermediate in the synthetic preparation of macromolecules such as the mycobacterium tuberculosis nonasaccharide. This nonasaccharide is an essential component of the cell wall of mycobacterium tuberculosis, the bacterium responsible for tuberculosis. The synthesis of this nonasaccharide can lead to the development of new drugs and therapies targeting tuberculosis.
Used in Research and Development:
.beta.-D-Glucopyranoside, phenyl 2,3,4,6-tetrakis-O-(phenylmethyl)-1-thiois also utilized in research and development for the study of carbohydrate chemistry and the development of new synthetic methods. Its unique structure and reactivity make it a valuable tool for exploring the properties and potential applications of complex carbohydrates and their derivatives.

Upstream product

• 2936-70-1 (2R,3S,4S,5R,6S)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol 
• 100-44-7 benzyl chloride 
• 100-39-0 benzyl bromide 
• 108-98-5 thiophenol 
• 13992-16-0 phenyl 2,3,4,6-tetra-O-acetyl-1-thio-α,β-D-glucopyranoside 
• 4196-35-4 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl bromide 
• 882-33-7 diphenyldisulfane 
• 1400565-90-3 C₄₀H₃₉BrO₅S 
• 6919-96-6 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 80300-30-7 1-O-acetyl-2,3,4,6-tetra-O-benzyl-D-glucopyranose 
• 14365-16-3 bis-(phenylthio)-dibutylstannane 
• 78890-59-2 Methoxy-acetic acid (2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester 
• 144-55-8 sodium hydrogencarbonate 
• 2936-70-1 (2R,3S,4S,5S,6R)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol 

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 
• 78890-53-6 ethyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside 
• 114967-51-0 isopropyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside 
• 114967-51-0 isopropyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside 
• 95189-55-2 3,4,5,7-Tetra-O-benzyl-2,6-anhydro-1-deoxy-D-glycero-D-gulo-heptitol 
• 4132-32-5 2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-D-glycero-D-ido-heptitol 
• 116501-51-0 (2R,3R,4R,5S,6S)-3,4,5-tris(benzyloxy)-2-(benzyloxymethyl)-6-ethyltetrahydro-2H-pyran 
• 116417-37-9 α-1,5-anhydro-1-C-ethyl-2,3,4,6-tetra-O-benzyl-D-glucitol 
• 112219-64-4 (2R,3R,4R,5S,6S)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-phenyltetrahydro-2H-pyran 
• 116417-38-0 (2R,3R,4R,5S,6R)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-phenyltetrahydro-2H-pyran 
• 139209-31-7 (1S,4S,5S,6R)-6-Benzyloxy-5-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-7-oxa-bicyclo[2.2.1]heptan-2-one 
• 139209-31-7 (1S,4S,5S,6R)-6-Benzyloxy-5-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-7-oxa-bicyclo[2.2.1]heptan-2-one 
• 55628-54-1 3,4,6-tri-O-benzyl-D-glucal 

Relevant articles and documents

Electrochemical Synthesis of Glycosyl Fluorides Using Sulfur(VI) Hexafluoride as the Fluorinating Agent

This manuscript describes the electrochemical synthesis of 17 different glycosyl fluorides in 73-98% yields on up to a 5 g scale that relies on the use of SF6 as an inexpensive and safe fluorinating agent. Cyclic voltammetry and related mechanistic studies carried out subsequently suggest that the active fluorinating species generated through the cathodic reduction of SF6 are transient under these reductive conditions and that the sulfur and fluoride byproducts are effectively scavenged by Zn(II) to generate benign salts.

Anomeric Thioglycosides Give Different Anomeric Product Distributions under NIS/TfOH Activation

The reaction of a series of anomeric thioglycosides with various glycosyl acceptors and N-iodosuccinimide/catalytic triflic acid was investigated with respect to reactivity and anomeric selectivity. In general, β-configured donors were found to give a more β-selective reaction outcome compared to their α-configured counterparts. The relative reactivity of various thioglycosides was measured through competition experiments, and the following order was established: phenyl, tolyl, methyl, ethyl, isopropyl, and 1-adamantyl.

How do Various Reaction Parameters Influence Anomeric Selectivity in Chemical Glycosylation with Thioglycosides and NIS/TfOH Activation?

The reaction of glycosyl donor phenyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-glucopyranoside with NIS/TfOH(cat.) was systematically studied under various reaction conditions. Neither the molecular sieve pore size nor amount of NIS activator was found to have a

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 %.

Ni-Catalyzed Suzuki-Miyaura Cross-Coupling of α-Oxo-vinylsulfones to Prepare C-Aryl Glycals and Acyclic Vinyl Ethers

We demonstrate that readily available and bench-stable α-oxo-vinylsulfones are competent electrophiles in Ni-catalyzed Suzuki-Miyaura cross-coupling reactions. The C-sulfone bond in the α-oxo-vinylsulfone motif is cleaved chemoselectively in these reactions, furnishing C-aryl glycals or acyclic vinyl ethers in high yields. These reactions proceed under mild conditions and tolerate a remarkable scope of heterocycles and functional groups. Preliminary mechanistic studies revealed the importance of an α-heteroatom in facilitating these transformations.

Ni-Catalyzed Suzuki-Miyaura Cross-Coupling of α-Oxo-vinylsulfones to Prepare C-Aryl Glycals and Acyclic Vinyl Ethers

We demonstrate that readily available and bench-stable α-oxo-vinylsulfones are competent electrophiles in Ni-catalyzed Suzuki-Miyaura cross-coupling reactions. The C-sulfone bond in the α-oxo-vinylsulfone motif is cleaved chemoselectively in these reactions, furnishing C-aryl glycals or acyclic vinyl ethers in high yields. These reactions proceed under mild conditions and tolerate a remarkable scope of heterocycles and functional groups. Preliminary mechanistic studies revealed the importance of an α-heteroatom in facilitating these transformations.

Dissection of the effects that govern thioglucoside and thiomannoside reactivity

Neighboring group effects were investigated in gluco- and manno-configured thioglycosides under NIS/TfOH activation. Donors possessing a 2-O-benzoyl group that are capable (1,2-trans) and incapable (1,2-cis) of exerting nucleophilic push were compared wit

Stereoretentive C(sp3)-S Cross-Coupling

We report a stereoretentive cross-coupling reaction of configurationally stable nucleophiles with disulfide and N-sulfenylsuccinimide donors promoted by Cu(I). We demonstrate the utility of this method in the synthesis of thioglycosides derived from simple alkyl and aryl thiols, thioglycosides, and in the glycodiversification of cysteine residues in peptides. These reactions operate well with carbohydrate substrates containing common protective groups and reagents with free hydroxyl and secondary amide functionalities under standardized conditions. Competition experiments in combination with computational DFT studies established that the putative anomeric intermediate is an organocopper species that is configurationally stable and resistant to epimerization due to its short lifetime. The subsequent reductive elimination from the Cu(III) intermediate is rapid and stereoretentive. Taken together, the glycosyl cross-coupling is ideally suited for late stage glycodiversification and bioconjugation under highly controlled installation of the aliphatic carbon-sulfur bonds.

On the generality of the superarmament of glycosyl donors

It was established that 2-O-benzoyl-3,4,6-tri-O-benzyl protected β-SEt, β-SPh and β-SBox glucosyl donors are not superarmed when using the NIS/TfOH promoter system, but instead have a similar reactivity as their classically armed tetra-O-benzyl protected glucosyl counterparts. The β-SBox 2-O-benzoyl-3,4,6-tri-O-benzyl glucosyl donor, however, was found to be superarmed under DMTST activation. Our studies have shown that the increased reactivity of the β-SBox 2-O-benzoyl-3,4,6-tri-O-benzyl glucosyl donor with DMTST activation could be a unique case, and that the high reactivity of glucosyl donors with the 2-O-benzoyl-3,4,6-tri-O-benzyl protection pattern is not general as earlier suggested.