62860-10-0

Basic information

• Product Name: 1-Thio-alpha-D-glucopyranose pentaacetate
• Synonyms: [(2R,3R,4S,5R,6R)-3,5-diacetyloxy-2-(acetyloxymethyl)-6-acetylsulfanyl-oxan-4-yl] acetate;2,3,4,6-Tetra-o-acetyl-1-S-acetyl-1- thio- glucopyranose;1-Thio-alpha-D-glucopyranose pentaacetate;α-D-pentaacetatethio Glucopyranose;AcGlcSAc
• CAS NO: 62860-10-0
• Molecular Formula: C₁₆H₂₂O₁₀S
• Molecular Weight: 406.41
• Mol File: 62860-10-0.mol
• Article Data: 32

Chemical Properties

• Melting Point: 121-122 °C
• Boiling Point: 468.1°Cat760mmHg
• Flash Point: 222.3°C
• Appearance: /
• Density: 1.32g/cm³
• Vapor Pressure: 6.17E-09mmHg at 25°C
• Refractive Index: 1.508
• CAS DataBase Reference: 1-Thio-alpha-D-glucopyranose pentaacetate(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Thio-alpha-D-glucopyranose pentaacetate(62860-10-0)
• EPA Substance Registry System: 1-Thio-alpha-D-glucopyranose pentaacetate(62860-10-0)

Safety Data

• Hazardous Substances Data: 62860-10-0(Hazardous Substances Data)

Usage

General Description

1-Thio-alpha-D-glucopyranose pentaacetate is a chemical compound that is structurally derived from glucose. It is a sulfur-containing sugar derivative with five acetyl groups attached to the glucose molecule. 1-Thio-alpha-D-glucopyranose pentaacetate is commonly used as a reagent in organic synthesis, particularly in the field of carbohydrate chemistry. It has also been studied for its potential applications in drug development and as a building block for the synthesis of more complex organic molecules. The acetyl groups on the molecule improve its solubility in organic solvents and make it a valuable tool for chemical reactions in a variety of laboratory settings.

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

• 507-09-5 tiolacetic acid 
• 4451-35-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl chloride 
• 108-24-7 acetic anhydride 
• 19879-84-6 tetraacetyl thioglucose 
• 83-87-4 D-glucose pentaacetate 
• 13035-49-9 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl iodide 
• 10387-40-3 potassium thioacetate 
• 4451-36-9 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl chloride 
• 22566-82-1 1-deoxy-1-thio-D-glucopyranose 
• 604-69-3 β-D-glucose pentaacetate 
• 50-99-7 D-glucose 
• 10593-29-0 sodium 1-thio-β-D-glucopyranoside 
• 3947-62-4 2,3,4,5-tetra-O-acetyl-D-glucopyranose 
• 6586-65-8 3,4,6-tri-O-acetyl-D-galactal 

Downstream Products

• 55474-17-4 Sodium; (2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-thiolate 
• 140654-62-2 (3R,S)-3,4-benzylidenedioxybutyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-glucopyranoside 
• 140654-63-3 (3R,S)-3-benzoyloxy-4-bromobutyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-glucopyranoside 
• 140654-64-4 methyl 2,3,6-tri-O-acetyl-4-S-<2-benzoyloxy-4-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosylthiobutyl)>-4-thio-α-D-glucopyranoside 
• 1138026-23-9 N-(2,4-dimethoxybenzyl)-1-S-(2,3,4,6-tetra-O-acetyl)-D-glucopyranosylsulfenamide 
• 1138026-22-8 N,N-bis(2,4-dimethoxybenzyl)-1-S-(2,3,4,6-tetra-O-acetyl)-D-glucopyranosylsulfenamide 
• 1138026-27-3 N-(4-methoxybenzyl)-1-S-(2,3,4,6-tetra-O-acetyl)-D-glucopyranosylsulfenamide 
• 6698-38-0 benzyl (2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl) disulfide 
• 6612-79-9 phenyl (2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl) disulfide 
• 10593-29-0 sodium 1-thio-β-D-glucopyranoside 

Relevant articles and documents

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.

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.

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.