N-<(9-fluorenylmethyl)oxy>carbonylvalyl-N-methylleucylalanine benzyl ester

Base Information

• Chemical Name: N-<(9-fluorenylmethyl)oxy>carbonylvalyl-N-methylleucylalanine benzyl ester
• CAS No.: 125714-54-7
• Molecular Formula: C₃₇H₄₅N₃O₆
• Molecular Weight: 627.781
• Mol file: 125714-54-7.mol

Synonyms:N-<(9-fluorenylmethyl)oxy>carbonylvalyl-N-methylleucylalanine benzyl ester

Chemical Property of N-<(9-fluorenylmethyl)oxy>carbonylvalyl-N-methylleucylalanine benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of N-<(9-fluorenylmethyl)oxy>carbonylvalyl-N-methylleucylalanine benzyl ester

There total 9 articles about N-<(9-fluorenylmethyl)oxy>carbonylvalyl-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: 61.0%

(S)-(9H-fluoren-9-yl)methyl 1-chloro-3-methyl-1-oxobutan-2-ylcarbamate (103321-53-5) + N-methyl-L-leucyl-L-alanine benzyl ester (81135-25-3) → N-<(9-fluorenylmethyl)oxy>carbonylvalyl-N-methylleucylalanine benzyl ester (125714-54-7)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 6 ℃;

DOI:10.1021/jo00296a061

Reference yield:

Fmoc-Val-OH (68858-20-8) + N-methyl-L-leucyl-L-alanine benzyl ester (81135-25-3) → N-<(9-fluorenylmethyl)oxy>carbonylvalyl-N-methylleucylalanine benzyl ester (125714-54-7)

Guidance literature:

With bis(2-oxo-3-oxazolidinyl)phosphoric acid chloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 ℃; Yield given;

DOI:10.1021/jo00296a061

Reference yield:

H-Ala-OBzl (17831-01-5) → N-<(9-fluorenylmethyl)oxy>carbonylvalyl-N-methylleucylalanine benzyl ester (125714-54-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 91.3 percent / 2,6-lutidine; BDMP / tetrahydrofuran / -10 - 20 °C

2: HNEt₂ / acetonitrile / 0.67 h

3: 0.532 g / BEP; DIEA / CH₂Cl₂ / -10 - 20 °C

With 2,6-dimethylpyridine; 2-bromo-1-ethylpyridin-1-ium tetrafluoroborate; diethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; acetonitrile; 1: Condensation / 2: Fmoc-deprotection / 3: Condensation;

DOI:10.1021/jo991687c

upstream raw materials:

Fmoc-Val-OH

N-methyl-L-leucyl-L-alanine benzyl ester

(S)-(9H-fluoren-9-yl)methyl 1-chloro-3-methyl-1-oxobutan-2-ylcarbamate

H-Ala-OBzl

Downstream raw materials:

N-methylleucylvalyl-N-methylleucylalanine benzyl ester

N-<(9-fluorenylmethyl)oxy>carbonyl-N-methylleucylvalyl-N-methylleucylalanine benzyl ester

H-Nva-Sar-(Me)Leu-Val-(Me)Leu-Ala-OBzl

N-[(9H-fluoren-9-ylmethoxy)carbonyl]norvalylsarcosyl-N-methylleucylvalyl-N-methylleucylalanine benzyl ester