benzyl (S)-4-(((9H-fluoren-9-yl)methoxy)carbonyl)amino-5-iodopentanoate

Base Information

• Chemical Name: benzyl (S)-4-(((9H-fluoren-9-yl)methoxy)carbonyl)amino-5-iodopentanoate
• CAS No.: 1172596-40-5
• Molecular Formula: C₂₇H₂₆INO₄
• Molecular Weight: 555.412
• Mol file: 1172596-40-5.mol

Synonyms:benzyl (S)-4-(((9H-fluoren-9-yl)methoxy)carbonyl)amino-5-iodopentanoate

Chemical Property of benzyl (S)-4-(((9H-fluoren-9-yl)methoxy)carbonyl)amino-5-iodopentanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl (S)-4-(((9H-fluoren-9-yl)methoxy)carbonyl)amino-5-iodopentanoate

There total 2 articles about benzyl (S)-4-(((9H-fluoren-9-yl)methoxy)carbonyl)amino-5-iodopentanoate 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: 100.0%

(S)-4-(9H-Fluoren-9-ylmethoxycarbonylamino)-5-hydroxy-pentanoic acid benzyl ester → benzyl (S)-4-(((9H-fluoren-9-yl)methoxy)carbonyl)amino-5-iodopentanoate (1172596-40-5)

Guidance literature:

With 1H-imidazole; iodine; triphenylphosphine;

DOI:10.1055/s-0029-1219584

Reference yield:

Fmoc-L-glutamic acid-g-benzyl ester (123639-61-2) → benzyl (S)-4-(((9H-fluoren-9-yl)methoxy)carbonyl)amino-5-iodopentanoate (1172596-40-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: isobutyl chloroformate; 4-methyl-morpholine / tetrahydrofuran / 1.17 h / -10 - 20 °C / Inert atmosphere

1.2: 0.25 h / -10 °C / Inert atmosphere

2.1: iodine; triphenylphosphine; 1H-imidazole / dichloromethane / 2 h

With 4-methyl-morpholine; 1H-imidazole; iodine; triphenylphosphine; isobutyl chloroformate; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo500911v

Reference yield: 90.0%

benzyl (S)-4-(((9H-fluoren-9-yl)methoxy)carbonyl)amino-5-iodopentanoate (1172596-40-5) → Fmoc-Glu(OBn)ψCH3

Guidance literature:

With palladium 10% on activated carbon; hydrogen; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; at 20 ℃; for 24h; under 2534.09 Torr; Reagent/catalyst; chemoselective reaction;

DOI:10.1021/jo500911v

upstream raw materials:

Fmoc-L-glutamic acid-g-benzyl ester

Downstream raw materials:

benzyl (S)-4-(((9H-fluoren-9-yl)methoxy)carbonyl)amino-5-azidobutanoate

Refernces

• 1、 Sureshbabu,Vishwanatha,Vasantha. "A simple synthesis of N β-Fmoc/Z-amino alkyl thiols and their use in the synthesis of N β-Fmoc/Z-amino alkyl sulfonic acids". body text. p. 1037 - 1042. Retrieved 2010/07/06.