N-<<(1,1-dimethylethyl)oxy>carbonyl>-cis-4-(phenylthio)-L-proline (trimethylsilyl)ethyl ester

Base Information

• Chemical Name: N-<<(1,1-dimethylethyl)oxy>carbonyl>-cis-4-(phenylthio)-L-proline (trimethylsilyl)ethyl ester
• CAS No.: 113949-43-2
• Molecular Formula: C₂₁H₃₃NO₄SSi
• Molecular Weight: 423.649

Synonyms:N-<<(1,1-dimethylethyl)oxy>carbonyl>-cis-4-(phenylthio)-L-proline (trimethylsilyl)ethyl ester

Chemical Property of N-<<(1,1-dimethylethyl)oxy>carbonyl>-cis-4-(phenylthio)-L-proline (trimethylsilyl)ethyl ester

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Technology Process of N-<<(1,1-dimethylethyl)oxy>carbonyl>-cis-4-(phenylthio)-L-proline (trimethylsilyl)ethyl ester

There total 3 articles about N-<<(1,1-dimethylethyl)oxy>carbonyl>-cis-4-(phenylthio)-L-proline (trimethylsilyl)ethyl ester 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: 81.0%

2-(Trimethylsilyl)ethanol (2916-68-9) + (2S,4S)-4-(phenylsulfanyl)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (83623-88-5) → N-<<(1,1-dimethylethyl)oxy>carbonyl>-cis-4-(phenylthio)-L-proline (trimethylsilyl)ethyl ester (113949-43-2)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; for 3h;

DOI:10.1021/jm00401a014

Reference yield:

(S)-4-phenylthio-L-proline (81653-77-2) → N-<<(1,1-dimethylethyl)oxy>carbonyl>-cis-4-(phenylthio)-L-proline (trimethylsilyl)ethyl ester (113949-43-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / Et₃N / H₂O; acetone / 24 h

2: 81 percent / 4-(dimethylamino)pyridine, dicyclohexylcarbodiimide / CH₂Cl₂ / 3 h

With dmap; triethylamine; dicyclohexyl-carbodiimide; In dichloromethane; water; acetone;

DOI:10.1021/jm00401a014

Reference yield:

2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile (58632-95-4) → N-<<(1,1-dimethylethyl)oxy>carbonyl>-cis-4-(phenylthio)-L-proline (trimethylsilyl)ethyl ester (113949-43-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / Et₃N / H₂O; acetone / 24 h

2: 81 percent / 4-(dimethylamino)pyridine, dicyclohexylcarbodiimide / CH₂Cl₂ / 3 h

With dmap; triethylamine; dicyclohexyl-carbodiimide; In dichloromethane; water; acetone;

DOI:10.1021/jm00401a014

upstream raw materials:

2-(Trimethylsilyl)ethanol

(2S,4S)-4-(phenylsulfanyl)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester

2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile

(S)-4-phenylthio-L-proline

Downstream raw materials:

(2S,4S)-4-Phenylsulfanyl-pyrrolidine-2-carboxylic acid 2-trimethylsilanyl-ethyl ester

1-[N-(1-(S)-ethoxycarbonyl-3-phenylpropyl)-L-alanyl]-4-(S)-(phenylthio)-L-proline

C₂₉H₄₀N₂O₅SSi

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