(S)-4-(4-Benzyloxycarbonylamino-2-oxo-2H-pyrimidin-1-yl)-2-tert-butoxycarbonylamino-butyric acid methyl ester

Base Information

• Chemical Name: (S)-4-(4-Benzyloxycarbonylamino-2-oxo-2H-pyrimidin-1-yl)-2-tert-butoxycarbonylamino-butyric acid methyl ester
• CAS No.: 182052-35-3
• Molecular Formula: C₂₂H₂₈N₄O₇
• Molecular Weight: 460.487
• Mol file: 182052-35-3.mol

Synonyms:(S)-4-(4-Benzyloxycarbonylamino-2-oxo-2H-pyrimidin-1-yl)-2-tert-butoxycarbonylamino-butyric acid methyl ester

Chemical Property of (S)-4-(4-Benzyloxycarbonylamino-2-oxo-2H-pyrimidin-1-yl)-2-tert-butoxycarbonylamino-butyric acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-4-(4-Benzyloxycarbonylamino-2-oxo-2H-pyrimidin-1-yl)-2-tert-butoxycarbonylamino-butyric acid methyl ester

There total 4 articles about (S)-4-(4-Benzyloxycarbonylamino-2-oxo-2H-pyrimidin-1-yl)-2-tert-butoxycarbonylamino-butyric acid methyl 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: 61.0%

methyl (2S)-4-bromo-2-[(tert-butoxycarbonyl)amino]butanoate (76969-87-4) + N-benzyloxycarbonyl cytosine (149411-91-6) → (S)-4-(4-Benzyloxycarbonylamino-2-oxo-2H-pyrimidin-1-yl)-2-tert-butoxycarbonylamino-butyric acid methyl ester (182052-35-3)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide;

DOI:10.1021/jo970111p

Reference yield:

tert-Butoxycarbonyl-L-homoserine DCHA salt (63491-82-7) → (S)-4-(4-Benzyloxycarbonylamino-2-oxo-2H-pyrimidin-1-yl)-2-tert-butoxycarbonylamino-butyric acid methyl ester (182052-35-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 65 percent / dimethylformamide / Ambient temperature

2: 75 percent / NBS, PPh₃ / CH₂Cl₂; pyridine / Ambient temperature

3: 61 percent / NaH / dimethylformamide

With N-Bromosuccinimide; sodium hydride; triphenylphosphine; In pyridine; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo970111p

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → (S)-4-(4-Benzyloxycarbonylamino-2-oxo-2H-pyrimidin-1-yl)-2-tert-butoxycarbonylamino-butyric acid methyl ester (182052-35-3)

Guidance literature:

Multi-step reaction with 2 steps

2: 61 percent / NaH / dimethylformamide

With sodium hydride; In N,N-dimethyl-formamide;

DOI:10.1021/jo970111p

upstream raw materials:

methyl (2S)-4-bromo-2-[(tert-butoxycarbonyl)amino]butanoate

N-benzyloxycarbonyl cytosine

tert-Butoxycarbonyl-L-homoserine DCHA salt

benzyl chloroformate

Downstream raw materials:

(S)-4-(4-Benzyloxycarbonylamino-2-oxo-2H-pyrimidin-1-yl)-2-tert-butoxycarbonylamino-butyric acid 2,5-dioxo-pyrrolidin-1-yl ester

[(S)-4-(4-Benzyloxycarbonylamino-2-oxo-2H-pyrimidin-1-yl)-2-tert-butoxycarbonylamino-butyrylamino]-acetic acid ethyl ester

[(S)-4-(4-Benzyloxycarbonylamino-2-oxo-2H-pyrimidin-1-yl)-2-tert-butoxycarbonylamino-butyrylamino]-acetic acid

(S)-N-tert-butoxycarbonyl-γ-(N4-benzoxycarbonyl-1-cytosinyl)homoalanine