(+)-Thiorphan

Base Information

• Chemical Name: (+)-Thiorphan
• CAS No.: 95909-00-5
• Molecular Formula: C12H15NO3S
• Molecular Weight: 253.322
• Hs Code.: 2930909090
• Mol file: 95909-00-5.mol

Synonyms:(S)-Thiorphan;S-Thiorphan;LY 171436;Glycine, N-[2-(mercaptomethyl)-1-oxo-3-phenylpropyl]-, (S)-;(+)-Thiorphan;

Chemical Property of (+)-Thiorphan

Chemical Property:

• Boiling Point: 524.0±50.0 °C (760 mmHg)
• PSA: 105.20000
• Density: 1.246±0.06 g/cm3 (20 °C, 760 mmHg)
• LogP: 1.36680

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (+)-Thiorphan

There total 11 articles about (+)-Thiorphan 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: 98.0%

N-<2(R)-<(benzoylthio)methyl>-1-oxo-3-phenylpropyl>glycine benzyl ester (100431-47-8) → (+)-Thiorphan (95909-00-5)

Guidance literature:

With sodium hydroxide; In methanol; at 0 - 20 ℃; for 2h;

DOI:10.1021/jm00155a027

Reference yield: 96.0%

N-<(2S)-2-<<(phenylmethyl)thio>methyl>-3-phenylpropanoyl>glycine benzyl ester (95841-17-1) → (+)-Thiorphan (95909-00-5)

Guidance literature:

With ammonia; sodium; In tetrahydrofuran; at -33 ℃; for 0.25h;

DOI:10.1021/jo00211a008

Reference yield:

2-[(benzoylthio)methyl]-3-phenylpropanoic acid (81110-58-9) → (+)-Thiorphan (95909-00-5)

Guidance literature:

Multi-step reaction with 3 steps

2: 88 percent / Et₃N, 1-hydroxybenzotriazole, N,N'-dicyclohexylcarbodiimide / CHCl₃; tetrahydrofuran / Ambient temperature

3: 98 percent / 1N aq. NaOH / methanol / 2 h / 0 - 20 °C

With sodium hydroxide; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; chloroform;

DOI:10.1021/jm00155a027

upstream raw materials:

N-<(2S)-2-<<(phenylmethyl)thio>methyl>-3-phenylpropanoyl>glycine benzyl ester

N-<2(R)-<(benzoylthio)methyl>-1-oxo-3-phenylpropyl>glycine benzyl ester

2-[(benzoylthio)methyl]-3-phenylpropanoic acid

(2S)-3-phenylcarbonylthio-2-phenylmethylpropionic acid

Refernces

• 1、 -. "beta -thiopropionyl-aminoacid derivatives and their use as beta -lactamase inhibitors". . . Retrieved 2008/06/13.
• 2、 Evans,Mathre,Scott. "Asymmetric synthesis of the enkephalinase inhibitor thiorphan". . p. 1830 - 1835. Retrieved 2007/10/02.