(S)-5-(acetylthio)-2-[N-(tert-butoxycarbonyl)amino]pentanoic acid benzyl ester

Base Information

• Chemical Name: (S)-5-(acetylthio)-2-[N-(tert-butoxycarbonyl)amino]pentanoic acid benzyl ester
• CAS No.: 247904-37-6
• Molecular Formula: C₁₉H₂₇NO₅S
• Molecular Weight: 381.493
• Mol file: 247904-37-6.mol

Synonyms:(S)-5-(acetylthio)-2-[N-(tert-butoxycarbonyl)amino]pentanoic acid benzyl ester

Chemical Property of (S)-5-(acetylthio)-2-[N-(tert-butoxycarbonyl)amino]pentanoic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-5-(acetylthio)-2-[N-(tert-butoxycarbonyl)amino]pentanoic acid benzyl ester

There total 5 articles about (S)-5-(acetylthio)-2-[N-(tert-butoxycarbonyl)amino]pentanoic acid benzyl 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: 91.0%

benzyl 2-(S)-[(tert-butoxycarbonyl)amino]-5-iodopentanoate (216753-82-1) + potassium thioacetate (10387-40-3) → (S)-5-(acetylthio)-2-[N-(tert-butoxycarbonyl)amino]pentanoic acid benzyl ester (247904-37-6)

Guidance literature:

In acetonitrile; at 20 ℃; for 1h; Inert atmosphere; Darkness;

DOI:10.1007/s00726-012-1352-5

Reference yield:

Boc-Glu-OBn (30924-93-7) → (S)-5-(acetylthio)-2-[N-(tert-butoxycarbonyl)amino]pentanoic acid benzyl ester (247904-37-6)

Guidance literature:

Multi-step reaction with 4 steps

1: Et₃N / tetrahydrofuran / 0.17 h / -10 °C

2: NaBH₄ / tetrahydrofuran; methanol / 0.33 h / -10 - 0 °C

3: Et₃N / CH₂Cl₂ / 2 h / 0 °C

4: acetone / 48 h / 20 °C

With sodium tetrahydroborate; triethylamine; In tetrahydrofuran; methanol; dichloromethane; acetone; 1: Condensation / 2: Reduction / 3: Condensation / 4: Substitution;

DOI:10.1021/jm9803727

Reference yield:

2-tert-butoxycarbonylamino-5-ethoxycarbonyloxy-5-oxo-pentanoic acid benzyl ester (105589-11-5) → (S)-5-(acetylthio)-2-[N-(tert-butoxycarbonyl)amino]pentanoic acid benzyl ester (247904-37-6)

Guidance literature:

Multi-step reaction with 3 steps

1: NaBH₄ / tetrahydrofuran; methanol / 0.33 h / -10 - 0 °C

2: Et₃N / CH₂Cl₂ / 2 h / 0 °C

3: acetone / 48 h / 20 °C

With sodium tetrahydroborate; triethylamine; In tetrahydrofuran; methanol; dichloromethane; acetone; 1: Reduction / 2: Condensation / 3: Substitution;

DOI:10.1021/jm9803727

upstream raw materials:

2-tert-butoxycarbonylamino-5-methanesulfonyloxy-pentanoic acid benzyl ester

potassium thioacetate

Boc-Glu-OBn

2-tert-butoxycarbonylamino-5-ethoxycarbonyloxy-5-oxo-pentanoic acid benzyl ester

Downstream raw materials:

(S)-5-(chlorosulfonyl)-2-[N-(tert-butoxycarbonyl)amino]pentanoic acid benzyl ester