19879-84-6

Basic information

• Product Name: 1-THIO-BETA-D-GLUCOSE TETRAACETATE
• Synonyms: 1-THIO-BETA-D-GLUCOSE TETRAACETATE;2,3,4,6-TETRA-O-ACETYL-1-THIO-BETA-D-GLUCOPYRANOSE;2,3,4,6-TETRA-O-ACETYL-1-THIO-BETA-D-THIOGLUCOPYRANOSE;BETA-D-THIOGLUCOSE TETRAACETATE;1-thio-beta-D-glucose 2,3,4,6-tetraacetate;1-THIO-B-D-GLUCOSE TETRAACETATE;.beta.-D-Glucopyranose, 1-thio-, 2,3,4,6-tetraacetate;2,3,4,6-Tetra-O-acetyl-b-D-thioglucopyranose
• CAS NO: 19879-84-6
• Molecular Formula: C₁₄H₂₀O₉S
• Molecular Weight: 364.37
• EINECS: 243-392-0
• Product Categories: Carbohydrates;substrate
• Mol File: 19879-84-6.mol
• Article Data: 70

Chemical Properties

• Melting Point: 115-117 °C(lit.)
• Boiling Point: 425.5 °C at 760 mmHg
• Flash Point: 298 °C
• Appearance: White crystalline powder
• Density: 1.32 g/cm³
• Vapor Pressure: 1.9E-07mmHg at 25°C
• Refractive Index: 1.502
• Storage Temp.: 2-8°C
• Solubility: Chloroform, Dichloromethane, Ethyl Acetate
• PKA: 8.42±0.70(Predicted)
• Water Solubility: Soluble in water and chloroform (50 mg/ml).
• BRN: 1440689
• CAS DataBase Reference: 1-THIO-BETA-D-GLUCOSE TETRAACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-THIO-BETA-D-GLUCOSE TETRAACETATE(19879-84-6)
• EPA Substance Registry System: 1-THIO-BETA-D-GLUCOSE TETRAACETATE(19879-84-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-36-26
• WGK Germany: 3
• Hazardous Substances Data: 19879-84-6(Hazardous Substances Data)

Usage

Description

1-Thio-beta-D-glucose tetraacetate is a synthetic intermediate that exists as a white crystalline powder. It is a modified form of glucose, with a sulfur atom replacing one of the hydroxyl groups and four acetate groups attached to it. This modification gives it unique chemical properties and makes it useful in various applications.

Uses

Used in Pharmaceutical Industry:
1-Thio-beta-D-glucose tetraacetate is used as a synthetic intermediate for the development of various pharmaceutical compounds. Its unique structure allows for the creation of novel molecules with potential therapeutic applications.
Used in Food Industry:
1-Thio-beta-D-glucose tetraacetate is used as an inhibitor of the Maillard reaction between glucose and glycine. The Maillard reaction is a complex series of chemical reactions that occur when reducing sugars, such as glucose, react with amino acids, like glycine, during cooking or food processing. This reaction is responsible for the browning of food and the development of flavors, but it can also lead to the formation of undesirable compounds. By using 1-thio-beta-D-glucose tetraacetate as an inhibitor, the Maillard reaction can be controlled, allowing for better management of food quality and safety.
Used in Chemical Research:
1-Thio-beta-D-glucose tetraacetate is also used in chemical research as a starting material for the synthesis of various complex organic compounds. Its unique structure makes it a valuable tool for exploring new chemical reactions and developing novel molecules with potential applications in various fields, including pharmaceuticals, materials science, and environmental science.

InChI:InChI=1/C14H20O9S/c1-6(15)19-5-10-11(20-7(2)16)12(21-8(3)17)13(14(24)23-10)22-9(4)18/h10-14,24H,5H2,1-4H3

Upstream product

• 57030-42-9 2-S-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-2-thiopseudourea hydrobromide 
• 40591-65-9 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiouronium bromide 
• 40591-65-9 2,3,4,6-tetra-O-acetylgalactopyranosyl-1-β-pseudothiourea hydrobromide 
• 252665-94-4 bis(2,3,4,6-tetra-O-acetyl-1-deoxy-1-thio-β-D-galactopyranosyl)-1,1'-disulfide 
• 40591-65-9 Acetic acid (2R,3S,4S,5R)-3,5-diacetoxy-2-acetoxymethyl-6-carbamimidoylsulfanyl-tetrahydro-pyran-4-yl ester; hydrobromide 
• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 
• 83-87-4 D-Mannose pentaacetate 
• 92217-67-9 1-S-acetyl-2,3,4,6-tetra-O-acetyl-1-deoxy-1-thio-α-D-mannopyranoside 
• 13242-53-0 acetobromomannose 
• 14227-52-2 2,3,4,6-tetra-O-acetyl-β-D-mannopyranosyl chloride 
• 857892-43-4 triphenylmethyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside 
• 25878-60-8 D-galactose pentaacetate 
• 380224-05-5 2,3,4,6-tetra-O-acetyl-1-thio-D-galactopyranose 
• 3068-32-4 1-bromo-2,3,4,6-tetra-O-acetyl-D-galactopyranose 

Downstream Products

• 13350-45-3 methyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside 
• 6806-56-0 O²,O³,O⁴,O⁶,S-Pentaacetyl-1-thio-β-D-glucopyranose 
• 6612-63-1 benzyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside 
• 64978-30-9 S-allyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside 
• 35785-63-8 2,3,4,6-tetra-O-acetyl-1-deoxy-1-(p-nitrobenzylthio)-β-D-glucopyranose 
• 5505-45-3 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside 
• 126647-39-0 Acetic acid (2S,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-(3-chloro-N-hydroxy-4-methoxy-benzimidoylsulfanyl)-tetrahydro-pyran-3-yl ester 
• 126647-40-3 Acetic acid (2S,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-(3,5-dichloro-N-hydroxy-4-methoxy-benzimidoylsulfanyl)-tetrahydro-pyran-3-yl ester 
• 74950-81-5 6-(benzyloxycarbonylamino)hexyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside 
• 74590-52-6 p-phenylbenzyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside 
• 76843-59-9 2,3,4,6-tetra-O-acetyl-1-S-diethylarsino-1-thio-β-D-glucopyranose 
• 85618-26-4 β-thiooctylperacetyl D-glucoside 
• 119824-61-2 4-((2S,3R,4S,5R,6R)-3,4,5-Triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-ylsulfanyl)-butyric acid benzyl ester 
• 119824-64-5 Acetic acid (2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-(3-benzyloxycarbonylamino-propylsulfanyl)-tetrahydro-pyran-4-yl ester 

Relevant articles and documents

Synthesis of cyclodextrin-based carbohydrate clusters by photoaddition reactions

The syntheses of homogeneous cyclodextrin-based carbohydrate clusters, persubstituted with β-D-thioglucosyl or D-thiolactosyl residues on either (a) the primary face, (b) the secondary face, or (c) both the primary and the secondary faces of their cyclodextrin tori, are described. The key step in the synthetic methodology, namely the attachment of the carbohydrate residues to the cyclodextrin torus, proceeds in moderate-good yields (42-70%) by the photoaddition of thiol groups, positioned at the anomeric centers of the carbohydrate residues, to allyl ether functions on the cyclodextrins. Facile removal of protecting groups then affords the free cluster compounds. Extensive 1-D and 2-D NMR spectroscopic investigations were performed on these compounds to determine their structures and establish their homogeneities, and a brief computer molecular modeling study allowed estimates of the dimensions of the clusters to be determined.

Synthesis and Biochemical Evaluation of an Artificial, Fluorescent Glucosinolate (GSL)

The synthesis of the first example of a fluorescent glucosinolate (GSL)–BODIPY conjugate based on an azide-containing artificial GSL precursor (GSL-N3) is reported. Biochemical evaluation of the artificial GSLs revealed that the compounds are converted to the corresponding isothiocyanates in the presence of myrosinase. Furthermore, myrosinase-catalyzed hydrolysis in the presence of plant specifier proteins yielded the expected alternative products, namely nitriles. The easy assembly of the fluorescent GSL–BODIPY conjugate by click chemistry from GSL-N3 holds potential for application as a fluorescence labeling tool to investigate GSL-associated processes.

Large-scale synthesis of thio-glucose-conjugated chlorin E6 for photodynamic therapy

Chlorin e6 is a heterocycle exhibiting spectral absorption in the 600-700 nm wavelength range used for photodynamic therapy (PDT). Herein, a sugar-conjugated chlorin e6 derivative was synthesized on a large scale. An alkyl spacer was fabricated by controlling the alkoxylation conditions between the thio-sugar and chlorin e6 and thio-glucose-conjugated chlorin e6 was successfully synthesized.

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.

8-Hydroxyquinoline glycoconjugates containing sulfur at the sugar anomeric position—synthesis and preliminary evaluation of their cytotoxicity

One of the main factors limiting the effectiveness of many drugs is the difficulty of their delivery to their target site in the cell and achieving the desired therapeutic dose. Moreover, the accumulation of the drug in healthy tissue can lead to serious side effects. The way to improve the selectivity of a drug to the cancer cells seems to be its conjugation with a sugar molecule, which should facilitate its selective transport through GLUT transporters (glucose transporters), whose overexpression is seen in some types of cancer. This was the idea behind the synthesis of 8-hydroxyquinoline (8-HQ) derivative glycoconjugates, for which 1-thiosugar derivatives were used as sugar moiety donors. It was expected that the introduction of a sulfur atom instead of an oxygen atom into the anomeric position of the sugar would increase the stability of the obtained glycoconjugates against untimely hydrolytic cleavage. The anticancer activity of new compounds was determined based on the results of the MTT cytotoxicity tests. Because of the assumption that the activity of this type of compounds was based on metal ion chelation, the effect of the addition of copper ions on cell proliferation was tested for some of them. It turned out that cancer cells treated with glycoconjugates in the presence of Cu2+ had a much slower growth rate compared to cells treated with free glycoconjugates in the absence of copper. The highest cytotoxic activity of the compounds was observed against the MCF-7 cell line.