benzyl (5S)-2-benzyl-2-(benzyloxycarbonyl)-5-<(tert-butyloxycarbonyl)amino>-7-methyl-4-oxooctanoate

Base Information

• Chemical Name: benzyl (5S)-2-benzyl-2-(benzyloxycarbonyl)-5-<(tert-butyloxycarbonyl)amino>-7-methyl-4-oxooctanoate
• CAS No.: 121157-65-1
• Molecular Formula: C₃₆H₄₃NO₇
• Molecular Weight: 601.74
• Mol file: 121157-65-1.mol

Synonyms:benzyl (5S)-2-benzyl-2-(benzyloxycarbonyl)-5-<(tert-butyloxycarbonyl)amino>-7-methyl-4-oxooctanoate

Chemical Property of benzyl (5S)-2-benzyl-2-(benzyloxycarbonyl)-5-<(tert-butyloxycarbonyl)amino>-7-methyl-4-oxooctanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl (5S)-2-benzyl-2-(benzyloxycarbonyl)-5-<(tert-butyloxycarbonyl)amino>-7-methyl-4-oxooctanoate

There total 5 articles about benzyl (5S)-2-benzyl-2-(benzyloxycarbonyl)-5-<(tert-butyloxycarbonyl)amino>-7-methyl-4-oxooctanoate 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:

N-tert-butoxycarbonyl-L-leucine (13139-15-6,53296-34-7) → benzyl (5S)-2-benzyl-2-(benzyloxycarbonyl)-5-<(tert-butyloxycarbonyl)amino>-7-methyl-4-oxooctanoate (121157-65-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 1) isobutyl chloroformate, TEA / 1) Et₂O, -15 deg C, 15 min, 2) Et₂O, -15 deg C, 2 h

2: 82 percent / HBr / diethyl ether / 5 °C

3: 1) NaH, HMPA, 2) HMPA / 1) DMF, 25 deg C, 40 min, 2) DMF, 25 deg C, 2 h

With N,N,N,N,N,N-hexamethylphosphoric triamide; TEA; hydrogen bromide; sodium hydride; isobutyl chloroformate; In diethyl ether;

DOI:10.1021/jm00126a039

Reference yield:

(3S)-3-<(tert-butoxy)carbonylamino>-1-diazo-5-methylhexan-2-one (52716-48-0) → benzyl (5S)-2-benzyl-2-(benzyloxycarbonyl)-5-<(tert-butyloxycarbonyl)amino>-7-methyl-4-oxooctanoate (121157-65-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 82 percent / HBr / diethyl ether / 5 °C

2: 1) NaH, HMPA, 2) HMPA / 1) DMF, 25 deg C, 40 min, 2) DMF, 25 deg C, 2 h

With N,N,N,N,N,N-hexamethylphosphoric triamide; hydrogen bromide; sodium hydride; In diethyl ether;

DOI:10.1021/jm00126a039

Reference yield:

malonic acid dibenzyl ester (15014-25-2) → benzyl (5S)-2-benzyl-2-(benzyloxycarbonyl)-5-<(tert-butyloxycarbonyl)amino>-7-methyl-4-oxooctanoate (121157-65-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 1) NaH, HMPA / 1) DMF, 25 deg C, 30 min, 2) 25 deg C, 3 h

2: 1) NaH, HMPA, 2) HMPA / 1) DMF, 25 deg C, 40 min, 2) DMF, 25 deg C, 2 h

With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydride;

DOI:10.1021/jm00126a039

upstream raw materials:

dibenzyl 2-benzylmalonate

N-((3S)-1-bromo-2-oxo-5-methyl-3-hexyl)-t-butoxycarboxamide

N-tert-butoxycarbonyl-L-leucine

malonic acid dibenzyl ester

Downstream raw materials:

(2RS,5S)-2-benzyl-5-<(tert-butyloxycarbonyl)amino>-7-methyl-4-oxooctanoic acid