N-Fmoc-3-iodo-L-alanine methyl ester

Base Information

• Chemical Name: N-Fmoc-3-iodo-L-alanine methyl ester
• CAS No.: 156017-42-4
• Molecular Formula: C19H18INO4
• Molecular Weight: 451.261
• European Community (EC) Number: 825-730-4
• Wikidata: Q76422680
• Mol file: 156017-42-4.mol

Synonyms:N-Fmoc-3-iodo-L-alanine methyl ester;156017-42-4;(R)-methyl 2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-iodopropanoate;methyl (2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-iodopropanoate;methyl (2R)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-iodopropanoate;MFCD13189980;SCHEMBL242522;CWUVRMHOLORRBM-KRWDZBQOSA-N;N-Fmoc-3-iodo-L-alaninemethylester;AKOS037647273;AS-73120;CS-0356399;D86331;EN300-6472813;methyl(2R)-2-(((9H-fluoren-9-ylmethoxy)carbonyl)amino)-3-iodopropanoate;(R)-METHYL 2-(((9H-FLUOREN-9-YL)METHOXY)CARBONYLAMINO)-3-IODOPROPANOATE

Chemical Property of N-Fmoc-3-iodo-L-alanine methyl ester

Chemical Property:

• XLogP3: 4.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 451.02806
• Heavy Atom Count: 25
• Complexity: 464

Purity/Quality:

99.3% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C(CI)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
• Isomeric SMILES: COC(=O)[C@H](CI)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13

Technology Process of N-Fmoc-3-iodo-L-alanine methyl ester

There total 5 articles about N-Fmoc-3-iodo-L-alanine 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: 92.0%

methyl (2S)-2-(((9H-fluoren-9-ylmethoxy)carbonyl)amino)-3-(((4-methylbenzene)sulfonyl)oxy)propanoate (229962-91-8) → 2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-iodo-propionic acid methyl ester (156017-42-4)

Guidance literature:

With sodium iodide; In acetone; at 20 ℃;

DOI:10.1039/b308750f

Reference yield:

N-(9H-fluoren-9-ylmethoxycarbonyl)-L-serine (73724-45-5) → 2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-iodo-propionic acid methyl ester (156017-42-4)

Guidance literature:

Multi-step reaction with 2 steps

1: sulfuric acid / 3 h / Reflux

2: triphenylphosphine; iodine; 1H-imidazole / dichloromethane / 2 h / 0 °C / Inert atmosphere

With 1H-imidazole; sulfuric acid; iodine; triphenylphosphine; In dichloromethane;

DOI:10.3998/ark.5550190.p009.803

Reference yield:

N-[(9-fluorenylmethoxy)carbonyl]-L-serine methyl ester (82911-78-2) → 2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-iodo-propionic acid methyl ester (156017-42-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / 4-dimethylaminopyridine; pyridine / 16 h / -5 °C

2: 84 percent / NaI / acetone / 48 h / 20 °C

With pyridine; dmap; sodium iodide; In acetone;

DOI:10.1021/ja068154n

upstream raw materials:

methyl (2S)-2-(((9H-fluoren-9-ylmethoxy)carbonyl)amino)-3-(((4-methylbenzene)sulfonyl)oxy)propanoate

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

N-[(9-fluorenylmethoxy)carbonyl]-L-serine methyl ester

N-(9H-fluoren-9-ylmethoxycarbonyl)-L-serine

Downstream raw materials:

Fmoc-(4-diethyl phosphonodifluoromethyl)-Phe-OMe

(2S)-(N-fluorenylmethoxycarbonylamino)-3-(pyrid-2'-yl)propionic acid

(2S)-2-(fluorenylmethoxycarbonylamino)-3-(5'-bromo-2'-pyridyl)propionic acid

(S)-2-{[(9H-fluoren-9-yl)methoxy]carbonylamino}-3-{4-[(diethoxyphosphoryl)difluoromethyl]phenyl}propanoic acid