130796-15-5

Basic information

• Product Name: 2,3,4,6-Tetra-O-acetyl-1-S-acetyl-1-thio-a-D-galactopyranoside
• Synonyms: 1,2,3,4,6-Penta-O-acetyl-a-D-thiogalactopyranose;2,3,4,6-Tetra-O-acetyl-1-S-acetyl-1-thio-α-D-galactopyranoside;1-Thio-
• CAS NO: 130796-15-5
• Molecular Formula: C₁₆H₂₂O₁₀S
• Molecular Weight: 406.406
• Product Categories: 13C & 2H Sugars;Carbohydrates & Derivatives;Sulfur & Selenium Compounds
• Mol File: 130796-15-5.mol
• Article Data: 35

Chemical Properties

• Melting Point: 95°C
• Boiling Point: 468.1±45.0 °C(Predicted)
• Appearance: /
• Density: 1.32±0.1 g/cm3(Predicted)
• Refractive Index: 1.509
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: 2,3,4,6-Tetra-O-acetyl-1-S-acetyl-1-thio-a-D-galactopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4,6-Tetra-O-acetyl-1-S-acetyl-1-thio-a-D-galactopyranoside(130796-15-5)
• EPA Substance Registry System: 2,3,4,6-Tetra-O-acetyl-1-S-acetyl-1-thio-a-D-galactopyranoside(130796-15-5)

Safety Data

• Hazardous Substances Data: 130796-15-5(Hazardous Substances Data)

Usage

Description

2,3,4,6-Tetra-O-acetyl-1-S-acetyl-1-thio-a-D-galactopyranoside is a complex organic compound with the chemical formula C18H26O9S. It is a white powder and is known for its role in the synthesis and evaluation of iNKT (invariant natural killer T) cell stimulators, specifically α-S-galactosylceramide.

Uses

Used in Pharmaceutical Industry:
2,3,4,6-Tetra-O-acetyl-1-S-acetyl-1-thio-a-D-galactopyranoside is used as a key intermediate in the synthesis of iNKT cell stimulators for the pharmaceutical industry. Its role is crucial in the development of therapeutic agents that can modulate the immune system and potentially treat various diseases, including cancer and autoimmune disorders.
Used in Research and Development:
In the field of research and development, 2,3,4,6-Tetra-O-acetyl-1-S-acetyl-1-thio-a-D-galactopyranoside is utilized for the synthesis and evaluation of α-S-galactosylceramide. 2,3,4,6-Tetra-O-acetyl-1-S-acetyl-1-thio-a-D-galactopyranoside serves as a valuable tool for scientists to study the mechanisms of iNKT cell activation and their potential applications in immunotherapy.
Chemical Properties:
The compound is a white powder with the molecular formula C18H26O9S. It is an acetylated and thio-modified derivative of α-D-galactopyranoside, which contributes to its unique chemical properties and reactivity in various synthetic processes.

InChI:InChI=1/C16H22O10S/c1-7(17)22-6-12-13(23-8(2)18)14(24-9(3)19)15(25-10(4)20)16(26-12)27-11(5)21/h12-16H,6H2,1-5H3/t12?,13-,14-,15-,16+/m0/s1

Upstream product

• 19879-84-6 O²,O³,O⁴,O⁶-Tetraacetyl-1-thio-D-glucose 
• 108-24-7 acetic anhydride 
• 5207-08-9 bis(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)disulfide 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 10387-40-3 potassium thioacetate 
• 507-09-5 tiolacetic acid 
• 4451-35-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl chloride 
• 604-69-3 β-D-glucose pentaacetate 
• 604-68-2 α-D-glucopyranose peracetylate 
• 75-36-5 acetyl chloride 
• 160621-19-2 2-(trimethylsilyl)ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside 
• 40591-65-9 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiouronium bromide 
• 47537-23-5 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiourea 
• 22566-82-1 1-deoxy-1-thio-D-glucopyranose 

Downstream Products

• 55474-17-4 Sodium; (2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-thiolate 
• 161016-86-0 methyl 2,3,6-tri-O-benzyl-4-deoxy-α-L-threo-hex-4-enopyranoside 
• 191485-96-8 methyl 2,3,6-tri-O-benzyl-4-S-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-4-thio-β-D-glucopyranoside 
• 22566-82-1 1-thio-β-D-glucopyranose 
• 19879-84-6 tetraacetyl thioglucose 
• 62778-20-5 sodium salt of 1-thio-α-D-glucopyranose 
• 874634-84-1 2-(tert-Butyl-dimethyl-silanyloxy)-4-[(2S,4aR,6R,7R,8R,8aR)-7,8-dihydroxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-ylsulfanyl]-butyronitrile 
• 870192-83-9 Acetic acid (2S,4aR,6R,7R,8S,8aS)-7-acetoxy-6-[3-(tert-butyl-dimethyl-silanyloxy)-3-cyano-propylsulfanyl]-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester 
• 870192-84-0 (2R,3R,4R,5R,6S)-4,5-Diacetoxy-3-[(2S,4aR,6R,7R,8S,8aS)-7,8-diacetoxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-ylsulfanyl]-6-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester 

Relevant articles and documents

Conversion of 2-(trimethylsilyl)ethyl sulfides into thioesters

Treatment of 2-(trimethylsilyl)ethyl sulfides with a carboxylic acid chloride and AgBF4 in CH2Cl2 furnishes the corresponding thioesters in high yields and purities. The conversion of 2-(trimethylsilyl)ethyl sulfides into synthetically versatile thioesters allows such sulfides to be used as sulfhydryl protective groups, since such sulfides are easily prepared and are stable towards many reaction conditions encountered in organic syntheses.

Stereoselective Thioconjugation by Photoinduced Thiol-ene Coupling Reactions of Hexo- and Pentopyranosyl d- and l-Glycals at Low-Temperature—Reactivity and Stereoselectivity Study

A comprehensive optimization and mechanistic study on the photoinduced hydrothiolation of different d- and l- hexo- and pentoglycals with various thiols was performed, at the temperature range of RT to ?120 °C. Addition of thiols onto 2-substituted hexoglycals proceeded with complete 1,2-cis-α-stereoselectivity in all cases. Hydrothiolation of 2-substituted pentoglycals resulted in mixtures of 1,2-cis-α- and -β-thioglycosides of varying ratio depending on the configuration of the reactants. Hydrothiolation of unsubstituted glycals at ?80 °C proceeded with excellent yields and, except for galactal, provided the axially C2-S-linked isomers with high selectivity. Cooling was always beneficial to the efficacy, increased the yields and in most cases significantly raised the stereoselectivity. The suggested mechanism explains the different conformational preferences of the intermediate carbon-centered radicals, which is a crucial factor in the stereoselectivity of the reactions.

Reaction of 1,2-trans-glycosyl acetates with thiourea: A new entry to 1-thiosugars

The reaction of 1,2-trans-glycosyl acetates with thiourea under boron trifluoride etherate catalysis affording acetylated S-glycosyl isothiourea derivatives is described. The isothiourea derivatives obtained can be readily transformed into the desired 1-thiosugar derivative by reaction with triethylamine and subsequent alkylation or acylation of the in situ formed 1-thioaldose.

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One pot synthesis of thio -glycosides via aziridine opening reactions

A one-pot aziridine opening reaction by glycosyl thiols generated in situ from the corresponding anomeric thio-acetates affords thio-glycosides with a pseudo-disaccharide structure and an N-linked tether. The scope of the one-pot aziridine opening reaction was explored on a series of mono- and disaccharides, creating a class of pseudo-glycosidic compounds with potential for further functionalization. Unexpected anomerization of glycosyl thiols was observed under the reaction conditions and the influence of temperature, base and solvent on the isomerization was investigated. Single isomers were obtained in good to acceptable yields for mannose, rhamnose and sialic acid derivatives. The class of thio-glycomimetics synthesized can potentially be recognized by various lectins, while presenting hydrolytic and enzymatic stability. The nitrogen functionality incorporated in the glycomimetics can be exploited for further functionalization, including tethering to linkers, scaffolds or peptide residues.

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.