130796-15-5

Usage

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 
• 2280-44-6 D-Glucose 

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 
• 62778-20-5 sodium salt of 1-thio-α-D-glucopyranose 
• 136591-19-0 Benzoic acid (E)-(R)-1-[(R)-1-amino-2-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-ylsulfanyl)-ethyl]-hexadec-2-enyl ester 
• 102527-08-2 S-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1->1)-(2R,3R,4E)-3-benzoyloxy-2-octadecanamido-4-octadecene-1-thiol 
• 1138026-23-9 N-(2,4-dimethoxybenzyl)-1-S-(2,3,4,6-tetra-O-acetyl)-D-glucopyranosylsulfenamide 

Relevant academic research and scientific papers

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.

Modular Synthesis of Aryl Thio/Selenoglycosides via the Catellani Strategy

We described a novel palladium-catalyzed domino procedure for the preparation of (hetero)aryl thio/selenoglycosides. Readily available (hetero)aryl iodides and easily accessible 1-thiosugars/1-selenosugars are utilized as the substrates. Meanwhile, 10 types of sugars are quite compatible with this reaction with good regio- and stereoselectivity, high efficiency, and broad applicability (up to 89%, 53 examples). This method enables the straightforward formation of the C(sp2)-S/Se bond of (hetero)aryl thio/selenoglycosides.

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.

STEREOSELECTIVE SYNTHESIS OF 1,2-TRANS-1-THIOGLYCOSES USING ALUMINIUM CHLORIDE: EVIDENCE FOR 1,2-CIS-1-CHLOROGLYCOPYRANOSYLPERACETATES AS THE ACTUAL REACTION INTERMEDIATES

Synthesis of 1,2-trans-1-thioglycosylacetates has been achieved in excellent yields from corresponding 1,2-trans-glycosylacetates using aluminium chloride via 1,2-cis-1-chloroglycopyranosylacetates with retention of configuration.

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.

A Sweet H2S/H2O2Dual Release System and Specific Protein S-Persulfidation Mediated by Thioglucose/Glucose Oxidase

H2S and H2O2 are two redox regulating molecules that play important roles in many physiological and pathological processes. While each of them has distinct biosynthetic pathways and signaling mechanisms, the crosstalk between these two species is also known to cause critical biological responses such as protein S-persulfidation. So far, many chemical tools for the studies of H2S and H2O2 have been developed, such as the donors and sensors for H2S and H2O2. However, these tools are normally targeting single species (e.g., only H2S or only H2O2). As such, the crosstalk and synergetic effects between H2S and H2O2 have hardly been studied with those tools. In this work, we report a unique H2S/H2O2 dual donor system by employing 1-thio-β-d-glucose and glucose oxidase (GOx) as the substrates. This enzymatic system can simultaneously produce H2S and H2O2 in a slow and controllable fashion, without generating any bio-unfriendly byproducts. This system was demonstrated to cause efficient S-persulfidation on proteins. In addition, we expanded the system to thiolactose and thioglucose-disulfide; therefore, additional factors (β-galactosidase and cellular reductants) could be introduced to further control the release of H2S/H2O2. This dual release system should be useful for future research on H2S and H2O2.

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.

Synthesis of Potential Glycosyl Transferase Inhibitors by Thio-Click Reactions

Leloir glycosyltransferases play an important role in many fundamental processes of living systems by catalyzing biological glycosylations. Neutral analogues of nucleotide sugars, as potential donor-substrate inhibitors of Leloir glycosyltransferases, are

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.

Preparation method and application of peracetyl-protected 1-thioglucose and glucose 1-mercaptan

The invention belongs to the technical field of medicine and sugar chemical synthesis, and particularly relates to a preparation method and application of peracetyl-protected 1-thioglucose and glucose1-mercaptan. The preparation method comprises the following steps of reacting peracetyl-protected glucose and potassium thioacetate in an organic solvent at the temperature of between normal temperature and 50 DEG C under the catalysis of boron trifluoride diethyl ether for 4-8 hours to obtain peracetyl-protected 1-thioglucose; and dissolving the prepared peracetyl-protected 1-thioglucose in dimethylformamide, and removing thioacetyl by using hydrazine hydrate to obtain peracetyl-protected glucose 1-mercaptan. The peracetyl-protected glucose 1-mercaptan can be used for further preparing auronofen and gliclazide thioglycoside analogues. The method disclosed by the invention is mild in reaction condition, simple and convenient to operate, low in synthesis cost, relatively green and high inyield, the auronofen is a medicine for treating rheumatic arthritis, and the gliflozin thioglycoside analogue is a potential medicine for treating type 2 diabetes mellitus.