50615-66-2

Basic information

• Product Name: 2,3,4,6-Tetra-O-acetyl-b-D-thiogalactopyranose
• Synonyms: 2,3,4,6-Tetra-O-acetyl-b-D-thiogalactopyranose;(2R,3S,4S,5R,6S)-2-(Acetoxymethyl)-6-mercaptotetrahydro-2H-pyran-3,4,5-triyl triacetate;b-D-Galactopyranose,1-thio-,2,3,4,6-tetraacetate;2,3,4,6-Tetra-O-acetyl-beta-D-1-thioglacatopyranoside
• CAS NO: 50615-66-2
• Molecular Formula: C₁₄H₂₀O₉S
• Molecular Weight: 364
• Mol File: 50615-66-2.mol

Chemical Properties

• Melting Point: 83 °C
• Boiling Point: 425.5±45.0 °C(Predicted)
• Appearance: /
• Density: 1.31±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 8.42±0.70(Predicted)
• CAS DataBase Reference: 2,3,4,6-Tetra-O-acetyl-b-D-thiogalactopyranose(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4,6-Tetra-O-acetyl-b-D-thiogalactopyranose(50615-66-2)
• EPA Substance Registry System: 2,3,4,6-Tetra-O-acetyl-b-D-thiogalactopyranose(50615-66-2)

Safety Data

• Hazardous Substances Data: 50615-66-2(Hazardous Substances Data)

Usage

Uses

Used in Biochemical Research:
2,3,4,6-Tetra-O-acetyl-b-D-thiogalactopyranose is used as a substrate in enzymatic reactions for studying the mechanisms and specificity of enzymes involved in carbohydrate metabolism. Its unique structure allows researchers to investigate the interactions between enzymes and their substrates, providing insights into the catalytic processes and the development of enzyme inhibitors or activators.
Used in Pharmaceutical Industry:
2,3,4,6-Tetra-O-acetyl-b-D-thiogalactopyranose is used as a component in the synthesis of carbohydrate-based drugs. Its specific properties make it a valuable building block for the development of new pharmaceutical compounds with potential therapeutic applications, such as anti-inflammatory, antiviral, or anticancer agents. 2,3,4,6-Tetra-O-acetyl-b-D-thiogalactopyranose's ability to interact with biological molecules and its potential to modulate biological processes make it a promising candidate for drug discovery and development.
Used in Drug Design and Development:
2,3,4,6-Tetra-O-acetyl-b-D-thiogalactopyranose is used as a structural template for designing new compounds with potential therapeutic applications. Its unique properties and interactions with biological systems provide a foundation for the development of innovative drugs that can target specific biological pathways or receptors, offering novel treatment options for various diseases and conditions.

Upstream product

• 14168-65-1 mannosan 
• 252665-94-4 bis(2,3,4,6-tetra-O-acetyl-1-deoxy-1-thio-β-D-galactopyranosyl)-1,1'-disulfide 
• 25878-60-8 D-galactose pentaacetate 
• 380224-05-5 2,3,4,6-tetra-O-acetyl-1-thio-D-galactopyranose 
• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 
• 572-09-8 acetobromogalactose 
• 3068-32-4 1-bromo-2,3,4,6-tetra-O-acetyl-D-galactopyranose 
• 3947-62-4 2,3,4,6-tetra-O-acetyl-α/β-D-galactopyranose 
• 10257-28-0 D-Galactose 
• 1666-13-3 diphenyl diselenide 
• 75801-94-4 tetra-O-acetyl-α-iodogalactopyranose 
• 86520-63-0 2,3,4,6-tetra-O-acetyl-α-galactopyranosyl trichloroacetimidate 
• 4163-60-4 β-D-galactose peracetate 
• 84062-53-3 2,3,4,6-tetra-O-acetylgalactopyranosyl-1-β-pseudothiourea hydrobromide 

Downstream Products

• 74590-54-8 2-phenylethyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside 
• 916453-24-2 Acetic acid (2R,3S,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(4-methoxy-phenyl)-diphenyl-methylsulfanyl]-tetrahydro-pyran-3-yl ester 
• 129729-59-5 (3,6/4,5)-4-bromo-3,5-dihydroxy-6-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosylthio)cyclohexene 
• 55722-48-0 methyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside 
• 854602-90-7 2,3,4,6-tetra-O-acetyl-1-S-(Z)-4-methoxybenzohydroximoyl-1-thio-β-D-galactopyranose 
• 916453-30-0 Acetic acid (2S,4aR,6S,7R,8S,8aS)-8-acetoxy-6-[(4-methoxy-phenyl)-diphenyl-methylsulfanyl]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester 
• 916453-29-7 (2R,3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-[(4-methoxy-phenyl)-diphenyl-methylsulfanyl]-tetrahydro-pyran 
• 857892-47-8 2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranose 
• 129729-60-8 Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-(4,6-diacetoxy-5-bromo-cyclohex-2-enylsulfanyl)-tetrahydro-pyran-3-yl ester 
• 1048006-13-8 2'-oxo-2'-phenylethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside 
• 1191092-87-1 benzyl 3-deoxy-4-S-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-4-thio-β-D-glycero-pentopyranosid-2-ulose 
• 1191092-88-2 benzyl 3-deoxy-4-S-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-4-thio-β-D-erythro-pentopyranoside 
• 1191092-89-3 benzyl 3-deoxy-4-S-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-4-thio-β-D-threo-pentopyranoside 

Relevant articles and documents

Improved Synthesis of 1-Glycosyl Thioacetates and Its Application in the Synthesis of Thioglucoside Gliflozin Analogues

An improved method to synthesize 1-glycosyl thioacetates was developed, where per-O-acetylated glycoses were allowed to directly react with potassium thioacetate (KSAc) in the presence of BF3 ? Et2O in ethyl acetate under mild conditions. This method not only overcomes the disadvantage of the traditional one-step method, which is that the odorous and toxic thioacetic acid has to be used, but also overcomes the disadvantage of the traditional two-step method, which is that the unstable intermediate, glycosyl halide, has to be synthesized from the per-O-acetylated glycose in advance. Based on this, the per-O-acetylated glucosyl disulfide and the per-O-acetylated glucosyl 1-thiol were efficiently synthesized in high yields (91 % and 90 % respectively) starting from per-O-acetylated glycoses in two-step without the need to isolate intermediate products. Through metal-catalyzed cross-coupling of per-O-acetylated glucosyl 1-thiol with aryl-iodide under very mild conditions, two thioglucoside gliflozin analogues were efficiently synthesized in high yields for the first time. These two thioglucoside gliflozin analogues were further confirmed to be stable to hydrolysis of β-glucosidase.

8-Hydroxyquinoline glycoconjugates containing sulfur at the sugar anomeric position—synthesis and preliminary evaluation of their cytotoxicity

One of the main factors limiting the effectiveness of many drugs is the difficulty of their delivery to their target site in the cell and achieving the desired therapeutic dose. Moreover, the accumulation of the drug in healthy tissue can lead to serious side effects. The way to improve the selectivity of a drug to the cancer cells seems to be its conjugation with a sugar molecule, which should facilitate its selective transport through GLUT transporters (glucose transporters), whose overexpression is seen in some types of cancer. This was the idea behind the synthesis of 8-hydroxyquinoline (8-HQ) derivative glycoconjugates, for which 1-thiosugar derivatives were used as sugar moiety donors. It was expected that the introduction of a sulfur atom instead of an oxygen atom into the anomeric position of the sugar would increase the stability of the obtained glycoconjugates against untimely hydrolytic cleavage. The anticancer activity of new compounds was determined based on the results of the MTT cytotoxicity tests. Because of the assumption that the activity of this type of compounds was based on metal ion chelation, the effect of the addition of copper ions on cell proliferation was tested for some of them. It turned out that cancer cells treated with glycoconjugates in the presence of Cu2+ had a much slower growth rate compared to cells treated with free glycoconjugates in the absence of copper. The highest cytotoxic activity of the compounds was observed against the MCF-7 cell line.

GOLD COMPOSITIONS AND METHODS OF USE THEREOF

Gold compounds and pharmaceutically acceptable salts thereof are disclosed. Certain compounds and salts are active as antibacterial, antifungal, and/or anti-parasitic agents. The disclosure provides pharmaceutical compositions containing the gold compounds. Methods of using the gold compounds to treat bacterial infections are disclosed.

POLYMER FOR DELIVERY OF BIOLOGICALLY ACTIVE MATERIALS

The present invention mainly relates to a polymer for delivery of biologically active materials, a complex and a method of synthesis thereof. The polymer comprises a poly(ethylene imine) and at least one monomer, each monomer comprising a modified sugar moiety, preferably galactose, comprising a sulphur atom or a nitrogen atom and a chemical moiety comprising a terminal epoxide for linking the polyethylene imine to the monomer, wherein the sulphur atom or the nitrogen atom links the modified sugar moiety to the chemical moiety. The biologically active material is preferably a gene, siRNA, mRNA, or plasmid DNA. Further disclosed is the medical use of said complex in treating a disease caused by a genetic disorder, for example cancer.

Combining Click Reactions for the One-Pot Synthesis of Modular Biomolecule Mimetics

Here, we report on the first combined one-pot use of the two so-called "click reactions": The thiol-ene coupling and the copper-catalyzed alkyne-azide cycloaddition. These reactions were employed in an alternating and one-pot fashion to combine appropriately functionalized monomeric carbohydrate building blocks to create mimics of trisaccharides and tetrasaccharides as single anomers, with only minimal purification necessary. The deprotected oligosaccharide mimics were found to bind both plant lectins and human galectin-3.

Bivalent glycoconjugates based on 1,5-diazabicyclo[3.3.0]octa-3,6-diene-2,8-dione (“bimane”) as a central scaffold

The heteroaromatic fused diazabicyclic “bimane” ring system, discovered four decades ago, is endowed with remarkable chemical and photophysical properties. No carbohydrate derivatives of bimanes have, however, been described thus far. Here we report on the syntheses of a range of bimanes decorated with various glycosyl residues. Mono- and disaccharide residues were attached to syn- or anti-bimane central cores via thio-, disulfido- or selenoglycosidic linkages to obtain novel fluorescent or nonfluorescent glycoconjugates. Cu(I)-catalyzed cycloaddition of glycosyl azides to a bimane diethynyl derivative furnished further bivalent glycoconjugates with sugar residues linked to the central bimane core via 1,2,3-triazole rings. We have determined the crystal and molecular structures of several glycosylated and non-glycosylated bimanes and report fluorescence data for the new compounds.

Synthesis and Structure-Activity Relationship Study of Antimicrobial Auranofin against ESKAPE Pathogens

Auranofin, an FDA-approved arthritis drug, has recently been repurposed as a potential antimicrobial agent; it performed well against many Gram-positive bacteria, including multidrug resistant strains. It is, however, inactive toward Gram-negative bacteria, for which we are in dire need of new therapies. In this work, 40 auranofin analogues were synthesized by varying the structures of the thiol and phosphine ligands, and their activities were tested against ESKAPE pathogens. The study identified compounds that exhibited bacterial inhibition (MIC) and killing (MBC) activities up to 65 folds higher than that of auranofin, making them effective against Gram-negative pathogens. Both thiol and the phosphine structures influence the activities of the analogues. The trimethylphosphine and triethylphosphine ligands gave the highest activities against Gram-negative and Gram-positive bacteria, respectively. Our SAR study revealed that the thiol ligand is also very important, the structure of which can modulate the activities of the AuI complexes for both Gram-negative and Gram-positive bacteria. Moreover, these analogues had mammalian cell toxicities either similar to or lower than that of auranofin.

Isopropyl - β - D thio-galactopyranoside synthetic method (by machine translation)

The present invention provides a kind of isopropyl - β - D thio-galactopyranoside synthetic method, namely the method for synthesis of IPTG. Comprises the following steps: five acetyl galactose as raw materials, with the thiourea reaction to obtain the acetyl S - galactose isothiourea fluoro salt, then with the pyrosulfites reaction to obtain the acetyl S - galactose, with isopropyl bromide reaction, the final deacetyl get the compound goal isopropyl - β - D thio-galactopyranoside. In the whole in the reaction process mainly selects the five acetyl galactose and isopropyl bromide as the raw material, not required to be selected smell, toxic isopropyl mercaptan, effectively avoiding harm to human health and the environment, in addition the invention has simple operation, high yield, purity and the like. Is suitable for industrial production. (by machine translation)

Development of photoswitchable inhibitors for β-galactosidase

Azobenzenes are of particular interest as a photochromic scaffold for biological applications because of their high fatigue resistance, their large geometrical change between extended (trans) and bent (cis) isomer, and their diverse synthetic accessibility. Despite their wide-spread use, there is no reported photochromic inhibitor of the well-investigated enzyme β-galactosidase, which plays an important role for biochemistry and single molecule studies. Herein, we report the synthesis of photochromic competitive β-galactosidase inhibitors based on the molecular structure of 2-phenylethyl β-d-thiogalactoside (PETG) and 1-amino-1-deoxy-β-d-galactose (β-d-galactosylamine). The thermally highly stable PETG-based azobenzenes show excellent photochromic properties in polar solvents and moderate to high photostationary states (PSS). The optimized compound 37 is a strong competitive inhibitior of β-galactosidase from Escherichia coli and its inhibition constant (Ki) changes between 60 nM and 290 nM upon irradiation with light. Additional docking experiments supported the observed structure-activity relationship.

Synthesis and anticancer activity of novel NHC-gold(I)-sugar complexes

Gold(I) complexes containing stabilising ligands such as phosphines or N-heterocyclic carbenes (NHCs) are known to be inhibitors of the enzyme thioredoxin reductase (TrxR) and therefore act as potential apoptosis-inducing anticancer drug candidates. The conjugation of biomolecules overexpressed in cancer cells to the gold complexes makes them semi-targeted metabolites. Auranofin, an anti-arthritis agent, encompasses this property and exhibits anti-tumour activities. The synthesis, characterization and biological evaluation of four novel N-heterocyclic carbene-gold(I)-thiosugar complexes derived from glucose, lactose and galactose is reported. The reactions of 1,3-dibenzyl-4,5-diphenyl-imidazol-2-ylidene gold(I) chloride (NHC?-Au-Cl) with pre-synthesized glycosyl thiols under mildly basic conditions gave the desired NHC-Au-thiosugar complexes in high to excellent yields (79–91%). The complexes retain the strong and redox-active Au-S bond contained in Auranofin. All complexes showed good solubility in biological media and were tested against the NCI 60 cancer cell panel for cytotoxicity. The synthesized NHC?-Au derivatives showed good activity in the medium to low micromolar region, while complex 2 showed activity in the low micromolar to nanomolar region against the tested cell lines. To provide a theoretical structure of 4, computational calculations were carried out based on the crystal structures of NHC-Au-SCN and NHC-Au-S-C6H4OMe.