(4S,5R,1'R,3'E)-2,2,3-trimethyl-5-(1'-methyl-3'-pentenyl)-4-(oxazolidinylcarbonyl)-L-2-aminobutyrylsarcosyl-N-methylleucylvalyl-N-methylleucylalanine benzyl ester

Base Information

• Chemical Name: (4S,5R,1'R,3'E)-2,2,3-trimethyl-5-(1'-methyl-3'-pentenyl)-4-(oxazolidinylcarbonyl)-L-2-aminobutyrylsarcosyl-N-methylleucylvalyl-N-methylleucylalanine benzyl ester
• CAS No.: 81135-32-2
• Molecular Formula: C₄₉H₈₁N₇O₉
• Molecular Weight: 912.224
• Mol file: 81135-32-2.mol

Synonyms:(4S,5R,1'R,3'E)-2,2,3-trimethyl-5-(1'-methyl-3'-pentenyl)-4-(oxazolidinylcarbonyl)-L-2-aminobutyrylsarcosyl-N-methylleucylvalyl-N-methylleucylalanine benzyl ester

Chemical Property of (4S,5R,1'R,3'E)-2,2,3-trimethyl-5-(1'-methyl-3'-pentenyl)-4-(oxazolidinylcarbonyl)-L-2-aminobutyrylsarcosyl-N-methylleucylvalyl-N-methylleucylalanine benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5R,1'R,3'E)-2,2,3-trimethyl-5-(1'-methyl-3'-pentenyl)-4-(oxazolidinylcarbonyl)-L-2-aminobutyrylsarcosyl-N-methylleucylvalyl-N-methylleucylalanine benzyl ester

There total 24 articles about (4S,5R,1'R,3'E)-2,2,3-trimethyl-5-(1'-methyl-3'-pentenyl)-4-(oxazolidinylcarbonyl)-L-2-aminobutyrylsarcosyl-N-methylleucylvalyl-N-methylleucylalanine benzyl 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:

N-(tert-Butyloxycarbonyl)-α-aminobutyrylsarcosine benzyl ester (81135-22-0) → (4S,5R,1'R,3'E)-2,2,3-trimethyl-5-(1'-methyl-3'-pentenyl)-4-(oxazolidinylcarbonyl)-L-2-aminobutyrylsarcosyl-N-methylleucylvalyl-N-methylleucylalanine benzyl ester (81135-32-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 96 percent / hydrogen / 10 percent Pd-C / ethanol

2: diisopropylethylamine, N,N'-bis(2-oxo-3-oxazolidinyl)phosphinic chloride / CH₂Cl₂ / 5 h / 0 °C

3: 90 percent / trifluoroacetic acid / CH₂Cl₂ / 14 h / -15 °C

4: 1) N-methylmorpholine, 1-hydroxybenzotriazole; 2) DCC / 1) THF; 2) 0 deg C, then 14 h room temperatur

With 4-methyl-morpholine; hydrogen; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium on activated charcoal; In ethanol; dichloromethane;

DOI:10.1021/jo00296a061

Reference yield:

C18H30N3O9P → (4S,5R,1'R,3'E)-2,2,3-trimethyl-5-(1'-methyl-3'-pentenyl)-4-(oxazolidinylcarbonyl)-L-2-aminobutyrylsarcosyl-N-methylleucylvalyl-N-methylleucylalanine benzyl ester (81135-32-2)

Guidance literature:

Multi-step reaction with 9 steps

1: diisopropylethylamine / CH₂Cl₂ / 5 °C

2: 50 percent trifluoroacetic acid / CH₂Cl₂ / 100 h / -18 - -13 °C

3: 78 percent / diisopropylethylamine, N,N'-bis(2-oxo-3-oxazolidinyl)phosphonic chloride / CH₂Cl₂ / 14 h / 5 °C

4: 100 percent / anisol, 5.8 M anhydrous HCl / dioxane / 1) 0 deg C, 2 h; 2) 5 deg C, 12 h

5: 1) diisopropylethylamine, N,N'-bis(2-oxo-3-oxazolidinyl)phosphinic chloride, 2) diisopropylethylamine / 1) CH₂Cl₂, 0 deg C, 2 h; 2) CH₂Cl₂, 6 deg C

6: 86 percent / trifluoroacetic acid / CH₂Cl₂ / 29 h / -18 - -13 °C / or from Fmoc-MeLeu-Val-MeLeu-Ala-OBzl with diethylamine in CH₃CN

7: diisopropylethylamine, N,N'-bis(2-oxo-3-oxazolidinyl)phosphinic chloride / CH₂Cl₂ / 5 h / 0 °C

8: 90 percent / trifluoroacetic acid / CH₂Cl₂ / 14 h / -15 °C

9: 1) N-methylmorpholine, 1-hydroxybenzotriazole; 2) DCC / 1) THF; 2) 0 deg C, then 14 h room temperatur

With 4-methyl-morpholine; hydrogenchloride; bis(2-oxo-3-oxazolidinyl)phosphoric acid chloride; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; benzotriazol-1-ol; methoxybenzene; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; In 1,4-dioxane; dichloromethane;

DOI:10.1021/jo00296a061

Reference yield:

H-Ala-OBzl (17831-01-5) → (4S,5R,1'R,3'E)-2,2,3-trimethyl-5-(1'-methyl-3'-pentenyl)-4-(oxazolidinylcarbonyl)-L-2-aminobutyrylsarcosyl-N-methylleucylvalyl-N-methylleucylalanine benzyl ester (81135-32-2)

Guidance literature:

Multi-step reaction with 9 steps

1: 78 percent / diisopropylethylamine, N,N'-bis(2-oxo-3-oxazolidinyl)phosphinic chloride / CH₂Cl₂ / 0 °C

2: diethylamine / acetonitrile

3: 78 percent / diisopropylethylamine, N,N'-bis(2-oxo-3-oxazolidinyl)phosphonic chloride / CH₂Cl₂ / 14 h / 5 °C

4: 100 percent / anisol, 5.8 M anhydrous HCl / dioxane / 1) 0 deg C, 2 h; 2) 5 deg C, 12 h

5: 1) diisopropylethylamine, N,N'-bis(2-oxo-3-oxazolidinyl)phosphinic chloride, 2) diisopropylethylamine / 1) CH₂Cl₂, 0 deg C, 2 h; 2) CH₂Cl₂, 6 deg C

6: 86 percent / trifluoroacetic acid / CH₂Cl₂ / 29 h / -18 - -13 °C / or from Fmoc-MeLeu-Val-MeLeu-Ala-OBzl with diethylamine in CH₃CN

7: diisopropylethylamine, N,N'-bis(2-oxo-3-oxazolidinyl)phosphinic chloride / CH₂Cl₂ / 5 h / 0 °C

8: 90 percent / trifluoroacetic acid / CH₂Cl₂ / 14 h / -15 °C

9: 1) N-methylmorpholine, 1-hydroxybenzotriazole; 2) DCC / 1) THF; 2) 0 deg C, then 14 h room temperatur

With 4-methyl-morpholine; hydrogenchloride; bis(2-oxo-3-oxazolidinyl)phosphoric acid chloride; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; benzotriazol-1-ol; methoxybenzene; diethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; In 1,4-dioxane; dichloromethane; acetonitrile;

DOI:10.1021/jo00296a061

upstream raw materials:

L-2-aminobutyryl-sarcosyl-N-methyl-L-leucyl-L-valyl-N-methyl-L-leucyl-L-alanine benzyl ester

(4S,5R,1'R,3'E)-2,2,3-trimethyl-5-(1'-methyl-3'-pentenyl)-4-oxazolidinecarboxylic acid

H-Ala-OBzl

methoxybenzyloxycarbonyl-Val

Downstream raw materials:

(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-(methylamino)-6-octenoyl-L-2-aminobutyrylsarcosyl-N-methylleucylvalyl-N-methylleucylalanine benzyl ester