S-Phenyl (betaR)-beta-hydroxybenzenepropanethioate

Base Information

• Chemical Name: S-Phenyl (betaR)-beta-hydroxybenzenepropanethioate
• CAS No.: 121788-80-5
• Molecular Formula: C₁₅H₁₄O₂S
• Molecular Weight: 258.341
• DSSTox Substance ID: DTXSID601258852
• Nikkaji Number: J2.779.518H
• Mol file: 121788-80-5.mol

Synonyms:DTXSID601258852;S-Phenyl (betaR)-beta-hydroxybenzenepropanethioate;(R)-3-Hydroxy-3-phenylpropanethioic acid S-phenyl ester;121788-80-5

Chemical Property of S-Phenyl (betaR)-beta-hydroxybenzenepropanethioate

Chemical Property:

• XLogP3: 3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 258.07145086
• Heavy Atom Count: 18
• Complexity: 255

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(CC(=O)SC2=CC=CC=C2)O
• Isomeric SMILES: C1=CC=C(C=C1)[C@@H](CC(=O)SC2=CC=CC=C2)O

Technology Process of S-Phenyl (betaR)-beta-hydroxybenzenepropanethioate

There total 5 articles about S-Phenyl (betaR)-beta-hydroxybenzenepropanethioate 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: 99.0%

S-phenyl hydrogen thiomalonate (4279-77-0) + benzaldehyde (100-52-7) → (R)-3-Hydroxy-3-phenyl-thiopropionic acid S-phenyl ester (121788-80-5)

Guidance literature:

benzaldehyde; With C₃₀H₃₁N₃O₃S; In tetrahydrofuran; tert-butyl methyl ether; at 20 ℃; for 0.0833333h;

S-phenyl hydrogen thiomalonate; In tetrahydrofuran; tert-butyl methyl ether; at 20 ℃; for 48h; Time; Reagent/catalyst; Temperature; Concentration; Solvent; enantioselective reaction;

DOI:10.1002/anie.201306297

Reference yield:

S-phenyl 3-hydroxy-3-phenylpropanethioate (42479-96-9) → (R)-3-Hydroxy-3-phenyl-thiopropionic acid S-phenyl ester (121788-80-5) + (S)-3-Hydroxy-3-phenyl-thiopropionic acid S-phenyl ester (149242-65-9)

Guidance literature:

With (1S,2R)-(+)-N-methylephedrine; In toluene; at 60 ℃;

DOI:10.1002/anie.200902373

Reference yield:

thiophenol (108-98-5) → (R)-3-Hydroxy-3-phenyl-thiopropionic acid S-phenyl ester (121788-80-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: diethyl ether / 6 h / 20 °C / Inert atmosphere

2.1: water; sodium hydrogencarbonate / Inert atmosphere

3.1: C₃₀H₃₁N₃O₃S / tert-butyl methyl ether; tetrahydrofuran / 0.08 h / 20 °C

3.2: 48 h / 20 °C

With C₃₀H₃₁N₃O₃S; water; sodium hydrogencarbonate; In tetrahydrofuran; diethyl ether; tert-butyl methyl ether;

DOI:10.1002/anie.201306297

upstream raw materials:

S-phenyl thioacetate

benzaldehyde

S-phenyl 3-hydroxy-3-phenylpropanethioate

S-phenyl hydrogen thiomalonate

Downstream raw materials:

methyl (R)-3-hydroxy-3-phenylpropanoate

methyl (S)-3-hydroxy-3-phenylpropionate