(4R)-3-[(2S)-2-({[(benzyloxy)carbonyl]amino}methyl)-4-(methylsulfanyl)-1-oxobutyl]-4-(1-methylethyl)-5,5-diphenyloxazolidin-2-one

Base Information

• Chemical Name: (4R)-3-[(2S)-2-({[(benzyloxy)carbonyl]amino}methyl)-4-(methylsulfanyl)-1-oxobutyl]-4-(1-methylethyl)-5,5-diphenyloxazolidin-2-one
• CAS No.: 637337-64-5
• Molecular Formula: C₃₂H₃₆N₂O₅S
• Molecular Weight: 560.714
• Mol file: 637337-64-5.mol

Synonyms:(4R)-3-[(2S)-2-({[(benzyloxy)carbonyl]amino}methyl)-4-(methylsulfanyl)-1-oxobutyl]-4-(1-methylethyl)-5,5-diphenyloxazolidin-2-one

Chemical Property of (4R)-3-[(2S)-2-({[(benzyloxy)carbonyl]amino}methyl)-4-(methylsulfanyl)-1-oxobutyl]-4-(1-methylethyl)-5,5-diphenyloxazolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R)-3-[(2S)-2-({[(benzyloxy)carbonyl]amino}methyl)-4-(methylsulfanyl)-1-oxobutyl]-4-(1-methylethyl)-5,5-diphenyloxazolidin-2-one

There total 5 articles about (4R)-3-[(2S)-2-({[(benzyloxy)carbonyl]amino}methyl)-4-(methylsulfanyl)-1-oxobutyl]-4-(1-methylethyl)-5,5-diphenyloxazolidin-2-one 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: 54.0%

(4R)-3-[(2S)-2-({[(benzyloxy)carbonyl]amino}methyl)-4-bromo-1-oxobutyl]-4-(1-methylethyl)-5,5-diphenyloxazolidin-2-one (637337-58-7) + sodium thiomethoxide (5188-07-8) → (4R)-3-[(2S)-2-({[(benzyloxy)carbonyl]amino}methyl)-4-(methylsulfanyl)-1-oxobutyl]-4-(1-methylethyl)-5,5-diphenyloxazolidin-2-one (637337-64-5)

Guidance literature:

In N,N-dimethyl-formamide; at 20 ℃; for 14h;

DOI:10.1002/hlca.200590157

Reference yield: 30.0%

benzyl N-(methoxymethyl) carbamate (94471-35-9) + (R)-4-isopropyl-3-(4-methylsulfanyl-1-oxobutyl)-5,5-diphenyloxazolidin-2-one (637337-48-5) → (R)-4-isopropyl-3-((R)-2-{[(methoxycarbonyl)amino]methyl}-4-(methylsulfanyl)-1-oxobutyl)-4-isopropyl-5,5-diphenyloxazolidin-2-one + (R)-4-isopropyl-3-((S)-2-{[(methoxycarbonyl)amino]methyl}-4-(methylsulfanyl)-1-oxobutyl)-4-isopropyl-5,5-diphenyloxazolidin-2-one (671233-56-0) + (R)-3-[(R)-2-{[(benzyloxy)carbonyl]amino}methyl-4-(methylsulfanyl)-1-oxopropyl]-4-isopropyl-5,5-diphenyloxazolidin-2-one + (4R)-3-[(2S)-2-({[(benzyloxy)carbonyl]amino}methyl)-4-(methylsulfanyl)-1-oxobutyl]-4-(1-methylethyl)-5,5-diphenyloxazolidin-2-one (637337-64-5)

Guidance literature:

With titanium tetrachloride; triethylamine; In dichloromethane; at 0 ℃; for 4h;

DOI:10.1002/hlca.200390337

Reference yield:

(R)-4-(1-methylethyl)-5,5-diphenyl-1,3-oxazolidin-2-one (191090-32-1) → (4R)-3-[(2S)-2-({[(benzyloxy)carbonyl]amino}methyl)-4-(methylsulfanyl)-1-oxobutyl]-4-(1-methylethyl)-5,5-diphenyloxazolidin-2-one (637337-64-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: BuLi / tetrahydrofuran / 0.17 h / -30 °C

1.2: 90 percent / tetrahydrofuran / 2 h / 0 °C

2.1: TiCl₄; Et₃N / CH₂Cl₂ / 0.5 h / -15 °C

2.2: TiCl₄ / CH₂Cl₂ / 3 h / 0 °C

3.1: 54 percent / dimethylformamide / 14 h / 20 °C

With n-butyllithium; titanium tetrachloride; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 2.1: Mannich reaction;

DOI:10.1002/hlca.200590157

upstream raw materials:

benzyl N-(methoxymethyl) carbamate

(R)-4-isopropyl-3-(4-methylsulfanyl-1-oxobutyl)-5,5-diphenyloxazolidin-2-one

(4R)-3-[(2S)-2-({[(benzyloxy)carbonyl]amino}methyl)-4-bromo-1-oxobutyl]-4-(1-methylethyl)-5,5-diphenyloxazolidin-2-one

sodium thiomethoxide

Downstream raw materials:

(S)-2-({[(benzyloxy)carbonyl]amino}methyl)-4-(methylsulfanyl)butanoic acid