13350-45-3

Basic information

• Product Name: METHYL 2,3,4,6-TETRA-O-ACETYL-BETA-D-THIOGLUCOPYRANOSIDE
• Synonyms: METHYL 2,3,4,6-TETRA-O-ACETYL-1-THIO-BETA-D-GLUCOPYRANOSIDE;METHYL 2,3,4,6-TETRA-O-ACETYL-BETA-D-THIOGLUCOPYRANOSIDE;methyl 2,3,4,6-tetra-O-acetyl-B-D-*thioglucopyran;METHYL 2,3,4,6-TETRA-O-ACETYL-B-D-*THIOG LUCOPYRANOS;methyl 2,3,4,6-tetra-o-acetyl-β-d-thioglucopyranoside;Methyl2,3,4,6-tetra-O-acetyl-b-D-thioglucopyranoside;Methyl 2,3,4,6-Tetra-O-acetyl-1-thio-β-D-galactopyranoside;Methyl 2,3,4,6-Tetra-O-acetyl-1-thio-β-D-glucopyranoside
• CAS NO: 13350-45-3
• Molecular Formula: C₁₅H₂₂O₉S
• Molecular Weight: 378.39
• Product Categories: Biochemistry;Glucose;O-Substituted Sugars;Sugars;Thioglycosides;Carbohydrates;Carbohydrates A to;Carbohydrates M-OBiochemicals and Reagents;Monosaccharide
• Mol File: 13350-45-3.mol
• Article Data: 23

Chemical Properties

• Melting Point: 91 °C
• Boiling Point: 440.5oC at 760 mmHg
• Flash Point: 206.9oC
• Appearance: /
• Density: 1.29g/cm3
• Vapor Pressure: 5.86E-08mmHg at 25°C
• Refractive Index: 1.502
• Storage Temp.: −20°C
• Solubility: soluble in Chloroform
• CAS DataBase Reference: METHYL 2,3,4,6-TETRA-O-ACETYL-BETA-D-THIOGLUCOPYRANOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 2,3,4,6-TETRA-O-ACETYL-BETA-D-THIOGLUCOPYRANOSIDE(13350-45-3)
• EPA Substance Registry System: METHYL 2,3,4,6-TETRA-O-ACETYL-BETA-D-THIOGLUCOPYRANOSIDE(13350-45-3)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 13350-45-3(Hazardous Substances Data)

Usage

General Description

Methyl 2,3,4,6-tetra-O-acetyl-beta-D-thioglucopyranoside is a chemical compound that belongs to the class of organic compounds known as thiosaccharides. These are saccharides in which a sugar unit has a thioether group substituted for a standard ether group. It is a derivative of cyclohexane and an S-glycoside. Methyl 2,3,4,6-tetra-O-acetyl-beta-D-thioglucopyranoside is specifically used as a synthetic intermediate in chemical reactions. Due to the acetyl groups, it has potent reactivity and the sulfide part in its structure provides a point for linking other molecules, making it useful for synthetic chemistry, especially in pharmaceutical applications. Its exact uses, however, may vary depending on the specific chemistry it is involved in.

InChI:InChI=1/C15H22O9S/c1-7(16)20-6-11-12(21-8(2)17)13(22-9(3)18)14(23-10(4)19)15(24-11)25-5/h11-15H,6H2,1-5H3/t11-,12-,13+,14-,15+/m1/s1

Upstream product

• 186581-53-3 diazomethane 
• 60-29-7 diethyl ether 
• 19879-84-6 O²,O³,O⁴,O⁶-Tetraacetyl-1-thio-D-glucose 
• 83-87-4 D-glucose pentaacetate 
• 17314-32-8 tributyl(methylthio)stannane 
• 74-93-1 methylthiol 
• 604-69-3 β-D-glucose pentaacetate 
• 47537-23-5 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiourea 
• 2280-44-6 D-Glucose 
• 108-24-7 acetic anhydride 
• 74-88-4 methyl iodide 
• 17720-64-8 N-acetoxyphthalimide 
• 6919-96-6 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 19879-84-6 tetraacetyl thioglucose 

Downstream Products

• 115678-26-7 methyl 2-O(2,3,4,6-tetra-O-acetyl-α-L-rhamnopyranosyl)-3,4-di-O-benzyl-α-L-rhamnopyranoside 
• 148905-71-9 methyl 2,3-di-O-benzoyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside 
• 854735-94-7 methyl 4,6-O-cyclohexylidene-2,3-di-O-(benzyl-d7)-1-thio-β-D-glucopyranoside 
• 854735-99-2 methyl 4,6-O-cyclohexylidene-2,3-di-O-benzyl-1-thio-β-D-glucopyranoside 
• 69895-14-3 methyl (2,3,4,6-tetra-O-acetyl-D-glucopyranosyl)-β-(1→6)-2,3,4-tri-O-benzoyl-α-D-glucopyranoside 
• 439-03-2 2,3,4,6-tetra-O-acetyl-1-fluoro-α-D-glucopyranose 
• 114967-51-0 isopropyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside 
• 62746-92-3 benzyl O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 71672-07-6 benzyl O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 114967-51-0 isopropyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside 
• 56632-57-6 methyl O-2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->6)-2,3,4-tri-O-benzyll-α-D-glucopyranoside 
• 55094-26-3 methyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl-(1-6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 115678-25-6 methyl 2-O-<2-O-(2,3,4,6-tetra-O-acetyl-α-L-rhamnopyranosyl)-3,4-di-O-benzyl-α-L-rhamnopyranosyl>-3,4-di-O-benzyl-α-L-rhamnopyranoside 
• 115678-24-5 methyl 2-O-(2,3,4,6-tetra-O-acetyl-α-L-mannopyranosyl)-3,4-di-O-benzyl-1-thio-α-L-rhamnopyranoside 

Relevant articles and documents

Synthesis of Branched Tetrasaccharide Derivatives of Schizophyllan-like β-Glucan

Branched tetrasaccharide derivatives as the repeating units of schizophyllan were synthesized using a common intermediate that had different protecting groups on the hydroxyl groups. Accordingly, β-1,3-disaccharide acceptors were efficiently glycosylated

Organophotoredox-Catalyzed Formation of Alkyl-Aryl and -Alkyl C-S/Se Bonds from Coupling of Redox-Active Esters with Thio/Selenosulfonates

A mild organophotoredox synthetic protocol for forming a Csp3-S/Se bond by reacting widespread redox-active esters with thio/selenosulfonates has been developed. The power of the synthetic manifold is fueled by an unprecedented broad substrate scope and wide functional group tolerance.

Synthesis of O-1- O-6 Substituted Positional Isomers of d -Glucose-Thioether Ligands and Their Ruthenium Polypyridyl Conjugates

A library of positional isomers of d-glucose (O-1-O-6) as ligands and their 11 light-active ruthenium conjugates has been synthesized. A protecting group strategy without the necessity of using palladium on carbon for the modification for the 2-O and 4-O position allows for the incorporation of sulfur donor atoms as ligands for transition metal complexes.