1-Thioglucose

Base Information

• Chemical Name: 1-Thioglucose
• CAS No.: 7534-35-2
• Molecular Formula: C₆H₁₂O₅S
• Molecular Weight: 196.224
• UNII: U1XQK5MJ1D
• DSSTox Substance ID: DTXSID10996788
• Nikkaji Number: J897.825E
• Wikidata: Q82988657
• Mol file: 7534-35-2.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 1-Thioglucose

Chemical Property:

• Vapor Pressure: 6.5E-15mmHg at 25°C
• Boiling Point: 560.8°Cat760mmHg
• Flash Point: 293°C
• Density: 1.611g/cm³
• XLogP3: -2.3
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 196.04054465
• Heavy Atom Count: 12
• Complexity: 142

Purity/Quality:

99%min. ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C(C(C(C(C(C=S)O)O)O)O)O
• Isomeric SMILES: C([C@H]([C@H]([C@@H]([C@H](C=S)O)O)O)O)O

Technology Process of 1-Thioglucose

There total 21 articles about 1-Thioglucose 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: 100.0%

tetraacetyl thioglucose (19879-84-6) → 1-thio-β-D-glucopyranose (22566-82-1,23558-19-2,49858-49-3,63073-99-4,135891-42-8,7534-35-2)

Guidance literature:

tetraacetyl thioglucose; With methanol; sodium methylate; at 20 ℃; for 0.166667h; Inert atmosphere;

In methanol;

DOI:10.1002/anie.200903135

Reference yield: 100.0%

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) → 1-thio-β-D-glucopyranose (22566-82-1,23558-19-2,49858-49-3,63073-99-4,135891-42-8,7534-35-2)

Guidance literature:

With sodium methylate; In methanol; for 1h; Inert atmosphere;

DOI:10.1002/anie.200704381

Reference yield: 70.0%

C6H11O8S2(1-)*Na(1+) → 1-thio-β-D-glucopyranose (22566-82-1,23558-19-2,49858-49-3,63073-99-4,135891-42-8,7534-35-2)

Guidance literature:

With tris-(2-carboxyethyl)-phosphine hydrochloride; In water-d2;

DOI:10.1016/j.carres.2020.108197

upstream raw materials:

D-Glucose

S-nitroso-1-thio-β-D-glucose

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

tetraacetyl thioglucose

Downstream raw materials:

phenyl 1-selenylsulfide-β-D-glucopyranoside

pyridine-2-thione

C₁₁H₁₅NO₅S₂

(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[(4-methoxyphenyl)thio]tetrahydro-2H-pyran-3,4,5-triol

Refernces

• 1、 Fairbanks, Antony J.. "Applications of Shoda's reagent (DMC) and analogues for activation of the anomeric centre of unprotected carbohydrates". . . Retrieved 2020/12/07.
• 2、 Commare, Bruno,Togni, Antonio. "Hypervalent Iodine Reagents: Thiol Derivatization with a Tetrafluoroethoxy Coumarin Residue for UV Absorbance Recognition". . . Retrieved 2017/05/26.