(4S,5S)-4-Benzyloxycarbonylamino-5-methyl-3-oxo-heptanoic acid tert-butyl ester

Base Information

• Chemical Name: (4S,5S)-4-Benzyloxycarbonylamino-5-methyl-3-oxo-heptanoic acid tert-butyl ester
• CAS No.: 135383-54-9
• Molecular Formula: C₂₀H₂₉NO₅
• Molecular Weight: 363.454
• Mol file: 135383-54-9.mol

Synonyms:(4S,5S)-4-Benzyloxycarbonylamino-5-methyl-3-oxo-heptanoic acid tert-butyl ester

Chemical Property of (4S,5S)-4-Benzyloxycarbonylamino-5-methyl-3-oxo-heptanoic acid tert-butyl ester

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5S)-4-Benzyloxycarbonylamino-5-methyl-3-oxo-heptanoic acid tert-butyl ester

There total 2 articles about (4S,5S)-4-Benzyloxycarbonylamino-5-methyl-3-oxo-heptanoic acid tert-butyl 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:

acetic acid tert-butyl ester (540-88-5) → (4S,5S)-4-Benzyloxycarbonylamino-5-methyl-3-oxo-heptanoic acid tert-butyl ester (135383-54-9)

Guidance literature:

Multi-step reaction with 2 steps

1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 1 h / -55 °C / Inert atmosphere

2: tetrahydrofuran; hexane / 3 h / -55 - 0 °C / Inert atmosphere

With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane;

DOI:10.1002/cmdc.202000497

Reference yield:

α-carbobenzoxy-L-isoleucine p-nitrophenyl ester (2130-99-6) + lithium tert-butyl acetate (1207973-75-8) → (4S,5S)-4-Benzyloxycarbonylamino-5-methyl-3-oxo-heptanoic acid tert-butyl ester (135383-54-9)

Guidance literature:

In tetrahydrofuran; hexane; at -55 - 0 ℃; for 3h; Inert atmosphere;

DOI:10.1002/cmdc.202000497

Reference yield: 90.0%

(4S,5S)-4-Benzyloxycarbonylamino-5-methyl-3-oxo-heptanoic acid tert-butyl ester (135383-54-9) → (3R,4S,5S)-4-Benzyloxycarbonylamino-3-hydroxy-5-methyl-heptanoic acid tert-butyl ester (135383-55-0)

Guidance literature:

With sodium tetrahydroborate; In methanol;

DOI:10.1016/S0040-4039(00)79932-1

upstream raw materials:

α-carbobenzoxy-L-isoleucine p-nitrophenyl ester

lithium tert-butyl acetate

acetic acid tert-butyl ester

Downstream raw materials:

(3R,4S,5S)-4-Benzyloxycarbonylamino-3-hydroxy-5-methyl-heptanoic acid tert-butyl ester

(3R,4S,5S)-4--3-methoxy-5-methylheptanoic acid

tert-Butyl (3R,4S,5S)-3-methoxy-4--5-methylheptanoate

(3R,4S,5S)-Dil-(2R,3R,4S)-Dap-(S)-Doe