6806-56-0

Basic information

• Product Name: b-D-Galactopyranose, 1-thio-,1,2,3,4,6-pentaacetate
• Synonyms: Galactopyranose,1-thio-, pentaacetate (7CI); Galactopyranose, 1-thio-, pentaacetate, b-D- (8CI); b-D-Galactopyranose, 1-thio-,pentaacetate (9CI); NSC 89877
• CAS NO: 6806-56-0
• Molecular Formula: C16H22 O10 S
• Molecular Weight: 406.411
• Mol File: 6806-56-0.mol
• Article Data: 30

Chemical Properties

• CAS DataBase Reference: b-D-Galactopyranose, 1-thio-,1,2,3,4,6-pentaacetate(CAS DataBase Reference)
• NIST Chemistry Reference: b-D-Galactopyranose, 1-thio-,1,2,3,4,6-pentaacetate(6806-56-0)
• EPA Substance Registry System: b-D-Galactopyranose, 1-thio-,1,2,3,4,6-pentaacetate(6806-56-0)

Safety Data

• Hazardous Substances Data: 6806-56-0(Hazardous Substances Data)

Upstream product

• 108-24-7 acetic anhydride 
• 40591-65-9 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiouronium bromide 
• 604-68-2 α-D-glucopyranose peracetylate 
• 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 
• 10387-40-3 potassium thioacetate 
• 604-69-3 β-D-glucose pentaacetate 
• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 
• 7534-35-2 1-deoxy-1-thio-D-galactopyranose 
• 75-36-5 acetyl chloride 
• 83-87-4 D-glucose pentaacetate 
• 50-99-7 D-glucose 
• 10593-29-0 sodium 1-thio-β-D-glucopyranoside 

Downstream Products

• 55474-17-4 Sodium; (2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-thiolate 
• 42891-22-5 1-thio-β-D-galactose (Na⁺-form) 
• 73962-00-2 Sodium; (2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-thiolate 
• 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 
• 136591-19-0 Benzoic acid (E)-(R)-1-[(R)-1-amino-2-((2S,3R,4S,5S,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-galactopyranosyl)-(1->1)-(2R,3R,4E)-3-benzoyloxy-2-octadecanamido-4-octadecene-1-thiol 
• 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 

Relevant articles and documents

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.

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.