(S)-2-((S)-4-Benzyloxycarbonylamino-4-tert-butoxycarbonyl-butyrylamino)-pentanoic acid tert-butyl ester

Base Information

• Chemical Name: (S)-2-((S)-4-Benzyloxycarbonylamino-4-tert-butoxycarbonyl-butyrylamino)-pentanoic acid tert-butyl ester
• CAS No.: 161878-62-2
• Molecular Formula: C₂₆H₄₀N₂O₇
• Molecular Weight: 492.613
• Mol file: 161878-62-2.mol

Synonyms:(S)-2-((S)-4-Benzyloxycarbonylamino-4-tert-butoxycarbonyl-butyrylamino)-pentanoic acid tert-butyl ester

Chemical Property of (S)-2-((S)-4-Benzyloxycarbonylamino-4-tert-butoxycarbonyl-butyrylamino)-pentanoic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-((S)-4-Benzyloxycarbonylamino-4-tert-butoxycarbonyl-butyrylamino)-pentanoic acid tert-butyl ester

There total 2 articles about (S)-2-((S)-4-Benzyloxycarbonylamino-4-tert-butoxycarbonyl-butyrylamino)-pentanoic 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) → (S)-2-((S)-4-Benzyloxycarbonylamino-4-tert-butoxycarbonyl-butyrylamino)-pentanoic acid tert-butyl ester (161878-62-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 70percent aq. perchloric acid / 48 h / Ambient temperature

2: 1.) isobutyl chloroformate, 4-methylmorpholine, / 1.) THF, -20 deg C, 10 min, 2.) THF, a) -20 deg C, 10 min, b) from -20 deg to RT

With 4-methyl-morpholine; perchloric acid; isobutyl chloroformate;

DOI:10.1021/jm00046a014

Reference yield:

(S)-2-(benzyloxycarbonylamino)pentanedioic acid tert-butyl ester (5891-45-2) + (S)-2-aminopentanoic acid tert-butyl ester (15911-75-8,158741-16-3) → (S)-2-((S)-4-Benzyloxycarbonylamino-4-tert-butoxycarbonyl-butyrylamino)-pentanoic acid tert-butyl ester (161878-62-2)

Guidance literature:

With 4-methyl-morpholine; isobutyl chloroformate; Yield given. Multistep reaction; 1.) THF, -20 deg C, 10 min, 2.) THF, a) -20 deg C, 10 min, b) from -20 deg to RT;

DOI:10.1021/jm00046a014

Reference yield:

(S)-2-((S)-4-Benzyloxycarbonylamino-4-tert-butoxycarbonyl-butyrylamino)-pentanoic acid tert-butyl ester (161878-62-2) → (S)-2-((S)-4-tert-Butoxycarbonyl-4-{4-[(2-methyl-4-oxo-3,4-dihydro-quinazolin-6-ylmethyl)-prop-2-ynyl-amino]-benzoylamino}-butyrylamino)-pentanoic acid tert-butyl ester (161878-76-8)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂ / 10percent Pd/C / tetrahydrofuran / 4 h / 760 Torr

2: 62 percent / diethyl cyanophosphoridate, Et₃N / dimethylformamide / 2 h / Ambient temperature

With diethyl cyanophosphoridate; hydrogen; triethylamine; palladium on activated charcoal; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/jm00046a014

upstream raw materials:

(S)-2-(benzyloxycarbonylamino)pentanedioic acid tert-butyl ester

(S)-2-aminopentanoic acid tert-butyl ester

acetic acid tert-butyl ester

Downstream raw materials:

(S)-2-((S)-4-tert-Butoxycarbonyl-4-{4-[(2-methyl-4-oxo-3,4-dihydro-quinazolin-6-ylmethyl)-prop-2-ynyl-amino]-benzoylamino}-butyrylamino)-pentanoic acid tert-butyl ester

Refernces