Carbamic acid, [(1S)-1-[1-hydroxy-2-oxo-2-[[(1R)-1-phenylethyl]amino]ethyl]pentyl]-, [1-[(2-pyrimidinylthio)methyl]cyclobutyl]methyl ester

Base Information

• Chemical Name: Carbamic acid, [(1S)-1-[1-hydroxy-2-oxo-2-[[(1R)-1-phenylethyl]amino]ethyl]pentyl]-, [1-[(2-pyrimidinylthio)methyl]cyclobutyl]methyl ester
• CAS No.: 568591-55-9
• Molecular Formula: C26H36N4O4S
• Molecular Weight: 500.662
• Mol file: 568591-55-9.mol

Synonyms:

Chemical Property of Carbamic acid, [(1S)-1-[1-hydroxy-2-oxo-2-[[(1R)-1-phenylethyl]amino]ethyl]pentyl]-, [1-[(2-pyrimidinylthio)methyl]cyclobutyl]methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Carbamic acid, [(1S)-1-[1-hydroxy-2-oxo-2-[[(1R)-1-phenylethyl]amino]ethyl]pentyl]-, [1-[(2-pyrimidinylthio)methyl]cyclobutyl]methyl ester

There total 5 articles about Carbamic acid, [(1S)-1-[1-hydroxy-2-oxo-2-[[(1R)-1-phenylethyl]amino]ethyl]pentyl]-, [1-[(2-pyrimidinylthio)methyl]cyclobutyl]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:

(3S)-3-amino-2-hydroxy-N-[(1R)-1-phenylethyl]heptanamide (497946-74-4) + C11H13ClN2O2S → {1-[(2-pyrimidinylsulfanyl)methyl]cyclobutyl}methyl (1S)-1-(1-hydroxy-2-oxo-2-{[(1R)-1-phenylethyl]amino}ethyl)pentylcarbamate (568591-55-9)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 0 ℃; for 6h;

DOI:10.1021/jm040107n

Reference yield:

[1-(hydroxymethyl)cyclobutyl]methanol (4415-73-0) → {1-[(2-pyrimidinylsulfanyl)methyl]cyclobutyl}methyl (1S)-1-(1-hydroxy-2-oxo-2-{[(1R)-1-phenylethyl]amino}ethyl)pentylcarbamate (568591-55-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: PPh₃; di-tert-butylazodicarboxylate / CH₂Cl₂ / 0.08 h / 20 °C

1.2: CH₂Cl₂ / 2 h / 20 °C

2.1: CH₂Cl₂; toluene / 16 h / 0 °C

3.1: N,N-diisopropylethylamine / tetrahydrofuran / 6 h / 0 °C

With di-tert-butyl-diazodicarboxylate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; toluene; 1.2: Mitsunobu reaction;

DOI:10.1021/jm040107n

Reference yield:

diethyl cyclobutane-1,1-dicarboxylate (3779-29-1) → {1-[(2-pyrimidinylsulfanyl)methyl]cyclobutyl}methyl (1S)-1-(1-hydroxy-2-oxo-2-{[(1R)-1-phenylethyl]amino}ethyl)pentylcarbamate (568591-55-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 95 percent / lithium aluminum hydride / diethyl ether; tetrahydrofuran / 3 h / 20 °C

2.1: PPh₃; di-tert-butylazodicarboxylate / CH₂Cl₂ / 0.08 h / 20 °C

2.2: CH₂Cl₂ / 2 h / 20 °C

3.1: CH₂Cl₂; toluene / 16 h / 0 °C

4.1: N,N-diisopropylethylamine / tetrahydrofuran / 6 h / 0 °C

With lithium aluminium tetrahydride; di-tert-butyl-diazodicarboxylate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; diethyl ether; dichloromethane; toluene; 2.2: Mitsunobu reaction;

DOI:10.1021/jm040107n

upstream raw materials:

(3S)-3-amino-2-hydroxy-N-[(1R)-1-phenylethyl]heptanamide

[1-(hydroxymethyl)cyclobutyl]methanol

diethyl cyclobutane-1,1-dicarboxylate

Benzoic acid (S)-2-benzyloxycarbonylamino-1-((R)-1-phenyl-ethylcarbamoyl)-hexyl ester