(2S,3R,4S,5R,6R)-2-(Ethylthio)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Base Information

• Chemical Name: (2S,3R,4S,5R,6R)-2-(Ethylthio)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
• CAS No.: 56245-60-4
• Molecular Formula: C8H16O5S
• Molecular Weight: 224.278
• Hs Code.: 2932990090
• European Community (EC) Number: 813-402-3
• DSSTox Substance ID: DTXSID70440378
• Nikkaji Number: J1.246.208E
• Mol file: 56245-60-4.mol

Synonyms:56245-60-4;(2S,3R,4S,5R,6R)-2-(Ethylthio)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol;ETHYL-BETA-D-THIOGALACTOPYRANOSIDE;ethyl 1-thio-beta-d-galactopyranoside;(2S,3R,4S,5R,6R)-2-ethylsulfanyl-6-(hydroxymethyl)oxane-3,4,5-triol;3zyh;SCHEMBL5899010;DTXSID70440378;Ethyl beta -D-thiogalactopyranoside;|A-D-Galactopyranoside, ethyl1-thio-;AKOS015919045;BATE-D-Galactopyranoside, ethyl1-thio-;Ethyl 1-Deoxy-1-thio-beta-D-galactopyranoside;A830974;Ethyl-beta-D-thiogalactopyranoside, >=98.0% (HPLC);2-ethylsulfanyl-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol;(2S,3R,4S,5R,6R)-2-(ETHYLSULFANYL)-6-(HYDROXYMETHYL)OXANE-3,4,5-TRIOL;G0S

Chemical Property of (2S,3R,4S,5R,6R)-2-(Ethylthio)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Chemical Property:

• Melting Point: 119-120oC
• Boiling Point: 440.767 °C at 760 mmHg
• PKA: 13.00±0.70(Predicted)
• Flash Point: 220.368 °C
• PSA: 115.45000
• Density: 1.437 g/cm³
• LogP: -1.46060
• Storage Temp.: −20°C
• Solubility.: Methanol, Water
• 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:

98%, ^*data from raw suppliers

Ethyl-β-D-thiogalactopyranoside ≥98.0% (HPLC) ^*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: Ethyl β-D-Thiogalactopyranoside (cas# 56245-60-4) is a compound useful in organic synthesis. Ethyl-β-D-thiogalactopyranoside is a derivitized thiogalactopyranoside structurally related to the gene expression inducer isopropyl-1-thio-β-D-galactopyranoside (IPTG).

Technology Process of (2S,3R,4S,5R,6R)-2-(Ethylthio)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

There total 41 articles about (2S,3R,4S,5R,6R)-2-(Ethylthio)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol 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 2,3,4,6-tetra-O-acetyl-1-thio-α-D-glycopyranoside

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

ethyl 1-thio-6-O-triphenylmethyl-α-D-mannopyranoside

Refernces

• 1、 -. "Beta-D-glucose short-chain fatty acid ester compound as well as preparation method and application thereof". Paragraph 0033; 0057; 0060. . Retrieved 2021/04/03.
• 2、 Alex, Catherine,Visansirikul, Satsawat,Demchenko, Alexei V.. "A versatile approach to the synthesis of glycans containing mannuronic acid residues". supporting information. p. 2731 - 2743. Retrieved 2021/04/07.