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
• Article Data: 46

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

General Description

2,3,4,6-Tetra-O-acetyl-b-D-thiogalactopyranose is a chemical compound that is a derivative of thiogalactopyranose, a type of sugar molecule. It is composed of four acetyl groups attached to the thiogalactopyranose molecule, which gives it specific properties and functions. 2,3,4,6-Tetra-O-acetyl-b-D-thiogalactopyranose is used in various biochemical and pharmaceutical applications, including as a substrate for enzymatic reactions and as a component in the synthesis of carbohydrate-based drugs. Its unique structure and properties make it valuable for studying the interactions and functions of sugar molecules in biological systems and for designing new compounds with potential therapeutic applications.

Upstream product

• 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 
• 3068-32-4 1-bromo-2,3,4,6-tetra-O-acetyl-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 
• 40591-65-9 Acetic acid (2R,3S,4S,5R)-3,5-diacetoxy-2-acetoxymethyl-6-carbamimidoylsulfanyl-tetrahydro-pyran-4-yl ester; hydrobromide 
• 62-55-5 thioacetamide 
• 6806-56-0 2,3,4,6-tetra-O-acetyl-1S-acetyl-1-thio-β-D-galactopyranose 
• 252665-94-4 bis(2,3,4,6-tetra-O-acetyl-1-deoxy-1-thio-β-D-galactopyranosyl)-1,1'-disulfide 

Downstream Products

• 74950-81-5 6-(benzyloxycarbonylamino)hexyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside 
• 74590-52-6 p-phenylbenzyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside 
• 74590-54-8 2-phenylethyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside 
• 51555-87-4 β-D-galactopyranosyl-(1→1)-1-thio-β-D-galactopyranoside 
• 854602-96-3 Acetic acid (5S,7R,8S,9S,10R)-8,9-diacetoxy-7-acetoxymethyl-3-(4-bromo-phenyl)-1,6-dioxa-4-thia-2-aza-spiro[4.5]dec-2-en-10-yl ester 
• 854602-92-9 Acetic acid (5S,7R,8S,9S,10R)-8,9-diacetoxy-7-acetoxymethyl-3-(4-methoxy-phenyl)-1,6-dioxa-4-thia-2-aza-spiro[4.5]dec-2-en-10-yl ester 
• 160707-24-4 Acetic acid (5S,7R,8S,9S,10R)-8,9-diacetoxy-7-acetoxymethyl-3-phenyl-1,6-dioxa-4-thia-2-aza-spiro[4.5]dec-2-en-10-yl ester 
• 857892-46-7 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-galactopyranose 

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.

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.

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.