62860-10-0

Usage

Uses

Used in Organic Synthesis:
1-Thio-alpha-D-glucopyranose pentaacetate is used as a reagent in organic synthesis for its ability to facilitate various chemical reactions. Its acetyl groups improve solubility, making it a valuable tool in a range of laboratory settings.
Used in Carbohydrate Chemistry:
In the field of carbohydrate chemistry, 1-Thio-alpha-D-glucopyranose pentaacetate is utilized as a reagent to support the synthesis of complex carbohydrate structures. Its unique properties allow for the creation of intricate molecular architectures that are essential in this specialized area of chemistry.
Used in Drug Development:
1-Thio-alpha-D-glucopyranose pentaacetate is studied for its potential applications in drug development. Its structural features and reactivity make it a candidate for the creation of new pharmaceutical compounds, particularly those that target specific biological pathways or mechanisms.
Used as a Building Block for Complex Organic Molecules:
1-Thio-alpha-D-glucopyranose pentaacetate also serves as a building block for the synthesis of more complex organic molecules. Its versatility in chemical reactions and compatibility with various organic solvents make it an ideal starting material for constructing a wide array of organic compounds with diverse applications.

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-/m1/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 
• 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 
• 19879-84-6 tetraacetyl thioglucose 
• 52485-06-0 3,4,6-tri-O-acetyl-D-glucal 
• 6586-65-8 3,4,6-tri-O-acetyl-D-galactal 
• 83-87-4 D-glucose pentaacetate 
• 507-09-5 tiolacetic acid 

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 
• 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 

Relevant academic research and scientific papers

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.

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.

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.

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.

Efficient generation of thiolate sugars from glycosyl Bunte salts and its application to S-glycoside synthesis

A one-pot aqueous solution method for synthesis of S-glycoside derivatives has been developed. Firstly, unprotected sugars were converted into glycosyl Bunte salts from which thiolate sugars can be generated efficiently using Na2S. The subsequent addition reaction with vinyl compounds or organic halides has successfully been demonstrated, giving rise to the corresponding S-glycosides.

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.

Synthesis of aromatic and indole alpha-glucosinolates

Aromatic and indole glucosinolates are important members of the glucosinolate family of compounds du to their potential medicinal properties. They are known to exert antioxidant and anti-carcinogenic activity either by the natural products themselves, or their metabolic products including indole-3-carbinol and isothiocyanates. Natural glucosinolates are all β-glucosinolates; however, α-glucosinolates are also promising compounds for medicinal applications and hence have to be produced synthetically for any bio-activity studies. Here we report on the successful synthesis of a series of α-glucosinolates: α-neoglucobrassicin, α-4-methoxyglucobrassicin, 2,3-dichlorophenyl-α-glucosinolate for the first time. Testing for anti-inflammatory properties of these synthetic GLs, however, did not yield the expected activity.

Dehydrative Thioglycosylation of 1-Hydroxyl Glycosides Catalyzed by In Situ-Generated AlI3

Thioglycosylation of 1-hydroxyl glycosides catalyzed by in situ-generated AlI3 from elemental aluminium and molecular iodine has been developed. This method provides an alternative route to access anomeric thioglycosides without the use of hazard Lewis acidic activators or per-modified activated thiol sources. The major advantages of this dehydrative procedure are environmental friendly, ease of operation, high anomeric diastereoselectivity, and mild reaction conditions.

Design, synthesis and biological evaluation of novel podophyllotoxin derivatives bearing 4β-disulfide/trisulfide bond as cytotoxic agents

A novel series of C-4β-disulfide/trisulfide-containing podophyllotoxin derivatives were designed, synthesized, and biologically evaluated for their cytotoxic activities against human cancer cell lines, including KB (Mouth Epidermal Carcinoma Cells) and KB/VCR (Vincristine-resistant Mouth Epidermal Carcinoma Cells). Most of these compounds exhibited promising moderate to good cytotoxic activities. In particular, some of them displayed even superior activities to that of etoposide, especially for KB/VCR cell lines, indicating that introduction of the disulfide/trisulfide moiety would be beneficial for overcoming the multi-drug resistant limitation of etoposide. Moreover, the metabolic evaluation of the most promising compound was further performed to reveal that disulfide bond can be stable in human plasma over 8 hours, indicating good potential of these compounds for in vivo anti-cancer activities.