Sodium (2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-thiolate

Base Information

• Chemical Name: Sodium (2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-thiolate
• CAS No.: 10593-29-0
• Molecular Formula: C6H12NaO5S
• Molecular Weight: 218.206
• Hs Code.: 29329990
• European Community (EC) Number: 234-200-6
• Nikkaji Number: J837.471F
• Mol file: 10593-29-0.mol

Synonyms:1-thio-beta-D-glucose;1-thioglucose;1-thioglucose, (D)-isomer;1-thioglucose, sodium salt;beta-D-thioglucose;sodium thioglucse

Chemical Property of Sodium (2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-thiolate

Chemical Property:

• Appearance/Colour: White to off-white solid
• Vapor Pressure: 2.66E-09mmHg at 25°C
• Melting Point: 173 °C
• Boiling Point: 432.6 °C at 760 mmHg
• Flash Point: 215.5 °C
• PSA: 90.15000
• LogP: -2.66680
• Storage Temp.: −20°C
• Solubility.: Water (Slightly), Methanol (Very Slightly, Heated, Sonicated)
• Water Solubility.: Soluble in water
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 1
• Exact Mass: 218.02248890
• Heavy Atom Count: 13
• Complexity: 160

Purity/Quality:

98%, ^*data from raw suppliers

b-D-Thioglucose sodium salt ^*data from reagent suppliers

Safty Information:

• Safety Statements: 6-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C(C1C(C(C(C(O1)[S-])O)O)O)O.[Na+]
• Isomeric SMILES: C([C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)[S-])O)O)O)O.[Na+]
• Uses: beta-D-Thioglucose sodium salt, is used in research and to treat rheumatoid arthritis. The biological mechanism is unknown. 1-Thio-β is often used as a carrier molecule for cell uptake of markers, polymers, and nanoparticles, and potentially useful synthetic reagent.

Technology Process of Sodium (2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-thiolate

There total 4 articles about Sodium (2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-thiolate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

C6H11O8S2(1-)*Na(1+) → sodium 1-thio-β-D-glucopyranoside (10593-29-0)

Guidance literature:

With sodiumsulfide nonahydrate; In water-d2; at 20 ℃; for 1h; Solvent;

DOI:10.1016/j.tetlet.2020.152198

Reference yield:

O2,O3,O4,O6,S-Pentaacetyl-1-thio-β-D-glucopyranose (6806-56-0,13639-50-4,51898-27-2,62860-10-0,63783-77-7,92217-67-9,92217-68-0,130796-15-5) → sodium 1-thio-β-D-glucopyranoside (10593-29-0)

Guidance literature:

With sodium methylate; In methanol; at 0 - 20 ℃;

DOI:10.1021/acs.jmedchem.9b00550

Reference yield:

tetraacetyl thioglucose (19879-84-6) → sodium 1-thio-β-D-glucopyranoside (10593-29-0)

Guidance literature:

With sodium methylate; In methanol; for 0.25h; Ambient temperature;

DOI:10.1002/(SICI)1099-0690(199905)1999:5<1143::AID-EJOC1143>3.0.CO;2-U

upstream raw materials:

tetraacetyl thioglucose

O²,O³,O⁴,O⁶,S-Pentaacetyl-1-thio-β-D-glucopyranose

D-glucose

Downstream raw materials:

2-S-β-D-glucopyranosyl-2-thio-β-D-glucopyranose

2-S-β-D-glucopyranosyl-2-thio-α-D-glucose

methyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-glucopyranoside

methyl (4,6-O-benzylidene-β-D-erythro-2,3-dideoxyhex-2-enopyranosyl)-(1->2)-3-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside

Refernces

• 1、 Wu, Bin,Yang, Xiaojian,Yan, Mingdi. "Synthesis and Structure-Activity Relationship Study of Antimicrobial Auranofin against ESKAPE Pathogens". . p. 7751 - 7768. Retrieved 2019/09/10.