Ethyl alpha-thioglucopyranoside

Base Information

• Chemical Name: Ethyl alpha-thioglucopyranoside
• CAS No.: 13533-58-9
• Molecular Formula: C₈H₁₆O₅S
• Molecular Weight: 224.278
• DSSTox Substance ID: DTXSID50706181
• Nikkaji Number: J3.030.150A
• Wikidata: Q82639466
• Mol file: 13533-58-9.mol

Synonyms:13533-58-9;ETHYL ALPHA-THIOGLUCOPYRANOSIDE;(2R,3R,4S,5S,6R)-2-ethylsulfanyl-6-(hydroxymethyl)oxane-3,4,5-triol;1-(Ethylthio)-1-deoxy-alpha-D-glucopyranose;ethyl 1-thio-alpha-d-glucopyranoside;Ethyl 1-thio--D-glucopyranoside;MFCD07369395;SCHEMBL7154429;DTXSID50706181;AKOS040767657;BS-45124;(2R,3R,4S,5S,6R)-2-(ETHYLSULFANYL)-6-(HYDROXYMETHYL)OXANE-3,4,5-TRIOL;(2R,3R,4S,5S,6R)-2-ethylsulfanyl-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol

Chemical Property of Ethyl alpha-thioglucopyranoside

Chemical Property:

• Melting Point: 156 °C
• Boiling Point: 440.8±45.0 °C(Predicted)
• PKA: 13.00±0.70(Predicted)
• PSA: 115.45000
• Density: 1.43±0.1 g/cm3(Predicted)
• LogP: -1.46060
• Storage Temp.: Hygroscopic, Refrigerator, under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly), Water (Slightly)
• XLogP3: -0.9
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 224.07184478
• Heavy Atom Count: 14
• Complexity: 179

Purity/Quality:

99% ^*data from raw suppliers

Ethylα-Thioglucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCSC1C(C(C(C(O1)CO)O)O)O
• Isomeric SMILES: CCS[C@@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O
• Uses: Α thioglucoside with antitumor potential.

Technology Process of Ethyl alpha-thioglucopyranoside

There total 35 articles about Ethyl alpha-thioglucopyranoside 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%

S-ethyl 2,3,4,6-tetra-O-acetyl-1-deoxy-1-thio-α-D-mannopyranoside (32934-24-0,41670-79-5,52645-73-5,55722-49-1,79389-52-9,99031-86-4,125354-48-5,126187-25-5) → ethyl 1-thio-α-D-mannopyranoside (7473-36-1,13533-58-9,36400-88-1,56245-60-4,73494-52-7,73804-33-8,128946-17-8,686299-00-3)

Guidance literature:

With sodium methylate; In methanol;

DOI:10.1016/S0040-4039(00)01497-0

Reference yield: 100.0%

ethyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-glycopyranoside (32934-24-0,41670-79-5,52645-73-5,55722-49-1,79389-52-9,99031-86-4,125354-48-5,126187-25-5) → (2R,3R,4S,5S,6R)-2-Ethylsulfanyl-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol (7473-36-1,13533-58-9,36400-88-1,56245-60-4,73494-52-7,73804-33-8,128946-17-8,686299-00-3)

Guidance literature:

With methanol; sodium methylate; for 20h; Ambient temperature;

DOI:10.1016/0957-4166(96)00066-3

Reference yield: 100.0%

ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside (32934-24-0,41670-79-5,52645-73-5,55722-49-1,79389-52-9,99031-86-4,125354-48-5,126187-25-5) → ethyl 1-thio-β-D-glucopyranoside (7473-36-1,13533-58-9,36400-88-1,56245-60-4,73494-52-7,73804-33-8,128946-17-8,686299-00-3)

Guidance literature:

With methanol; sodium methylate; for 20h; Ambient temperature;

DOI:10.1016/0957-4166(96)00066-3

upstream raw materials:

ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside

ethanethiol

β-D-glucose pentaacetate

ethyl iodide

Downstream raw materials:

ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside

ethyl 4,6-O-benzylidene-1-thio-β-D-glucopyranoside

ethyl 4,6-O-benzylidene-1-thio-β-D-glucopyranoside

1-deoxy-1-(S-ethyl)-2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside