5-Thio-D-Glucose

Base Information

• Chemical Name: 5-Thio-D-Glucose
• CAS No.: 20408-97-3
• Deprecated CAS: 119663-50-2
• Molecular Formula: C6H12 O5 S
• Molecular Weight: 196.224
• Hs Code.: 2930909090
• European Community (EC) Number: 243-798-8
• UNII: 3PRV1384UO
• DSSTox Substance ID: DTXSID701031304
• Nikkaji Number: J122.418B
• Wikidata: Q27257877
• ChEMBL ID: CHEMBL3322300
• Mol file: 20408-97-3.mol

Synonyms:5-thio-D-glucose;5-thio-D-glucose, 6-phosphate;5-thioglucose

Chemical Property of 5-Thio-D-Glucose

Chemical Property:

• Vapor Pressure: 4.09E-08mmHg at 25°C
• Melting Point: 135-138 °C(lit.)
• Refractive Index: 1.5060 (estimate)
• Boiling Point: 463.3 °C at 760 mmHg
• PKA: 9.11±0.10(Predicted)
• Flash Point: 234 °C
• PSA: 136.79000
• Density: 1.503 g/cm³
• LogP: -2.44130
• Storage Temp.: 2-8°C
• Solubility.: Soluble in Water (up to 15 mg/ml)
• Water Solubility.: Miscible with water.
• XLogP3: -2
• 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:

98%, ^*data from raw suppliers

5-Thio-D-glucose ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Uses -> Biochemical Research
• Canonical SMILES: C(C(C(C(C(C=O)O)O)O)S)O
• Isomeric SMILES: C([C@H]([C@H]([C@@H]([C@H](C=O)O)O)O)S)O
• Description: 5-Thio-D-glucose (20408-97-3) is a potent competitive inhibitor of the cellular transport of glucose and glucose-mediated insulin release.1 May be used to induce a state of glucose deprivation in laboratory animals.2 Stimulates feeding in rat models.3? Induces Alzheimer-like changes in frontal cortex and hippocampus in rats.4? Elevates renal TGF-b1 at a dose that does not prevent streptozotocin diabetes in rats.5
• Uses: 5-Thio-D-glucose (cas# 20408-97-3) is a compound useful in organic synthesis.

Technology Process of 5-Thio-D-Glucose

There total 1 articles about 5-Thio-D-Glucose 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:

→ 5-Thio-D-glucose (20408-97-3)

Guidance literature:

Reference yield: 75.0%

5-Thio-D-glucose (20408-97-3) + trityl chloride (76-83-5) → 5-deoxy-5-thio-6-O-triphenylmethylglucopyranose

Guidance literature:

With pyridine; at 60 ℃; for 23h;

DOI:10.1016/j.bmc.2005.05.028

Reference yield:

5-Thio-D-glucose (20408-97-3) → 4-O-[3',4',6'-tri-O-acetyl-5'-deoxy-5'-thio-α-D-glucopyranosyl]-1,2,3,6-tetra-O-benzoyl-5-deoxy-5-thio-α-D-glucopyranose

Guidance literature:

Multi-step reaction with 2 steps

1: 65.2 mg / pyridine / 1.5 h / 20 °C

2: 0.1 mg / triethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 2 h / -78 °C

With pyridine; triethylsilyl trifluoromethyl sulfonate; In dichloromethane;

DOI:10.1016/j.bmc.2005.05.028