benzyl (S)-2-<(tert-butyloxycarbonyl)amino>-5-acetoxypentanoate

Base Information

• Chemical Name: benzyl (S)-2-<(tert-butyloxycarbonyl)amino>-5-acetoxypentanoate
• CAS No.: 91230-02-3
• Molecular Formula: C₁₉H₂₇NO₆
• Molecular Weight: 365.426
• Mol file: 91230-02-3.mol

Synonyms:benzyl (S)-2-<(tert-butyloxycarbonyl)amino>-5-acetoxypentanoate

Chemical Property of benzyl (S)-2-<(tert-butyloxycarbonyl)amino>-5-acetoxypentanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl (S)-2-<(tert-butyloxycarbonyl)amino>-5-acetoxypentanoate

There total 2 articles about benzyl (S)-2-<(tert-butyloxycarbonyl)amino>-5-acetoxypentanoate 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: 86.0%

Boc-L-proline benzyl ester (37787-77-2) + (S)-2-[N-(tert-butoxycarbonyl)amino]-5-hydroxypentanoic acid benzyl ester (91229-97-9) → benzyl (S)-2-<(tert-butyloxycarbonyl)amino>-5-acetoxypentanoate (91230-02-3)

Guidance literature:

With pyridine; In dichloromethane; for 4h; Ambient temperature;

DOI:10.1021/jo00193a016

Reference yield:

α-benzyl Nα-(tert-butyloxycarbonyl)-L-glutamate (30924-93-7) → benzyl (S)-2-<(tert-butyloxycarbonyl)amino>-5-acetoxypentanoate (91230-02-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 30 percent / B₂H₆ / tetrahydrofuran / 4 h / 0 °C

2: 86 percent / pyridine / CH₂Cl₂ / 4 h / Ambient temperature

With pyridine; diborane; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo00193a016

Reference yield:

benzyl (S)-2-<(tert-butyloxycarbonyl)amino>-5-acetoxypentanoate (91230-02-3) → 1-(benzyloxy)-3-<(tert-butyloxycarbonyl)amino>-2-piperidone (91279-50-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 92 percent / H₂ / 5percent Pd/C / ethanol; H₂O / 12 h / Ambient temperature

2: 88 percent / NEt₃ / 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride / CH₂Cl₂ / 12 h / Ambient temperature

3: 99 percent / 1N NaOH / acetone / 1 h / Ambient temperature

4: 64 percent / diethyl azodicarboxylate (DEAD) / PPh₃ / tetrahydrofuran / 24 h / Ambient temperature

With sodium hydroxide; hydrogen; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; water; acetone;

DOI:10.1021/jo00193a016

upstream raw materials:

Boc-L-proline benzyl ester

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

α-benzyl N^α-(tert-butyloxycarbonyl)-L-glutamate

Downstream raw materials:

1-(benzyloxy)-3-<(tert-butyloxycarbonyl)amino>-2-piperidone

(S)-O-benzyl 2-<(tert-butyloxycarbonyl)amino>-5-hydroxypentanohydroxamate

O-benzyl (S)-2-<(tert-butyloxycarbonyl)amino>-5-acetoxypentanohydroxamate