N-Fmoc-3-iodo-L-alanine tert-butyl ester

Base Information

• Chemical Name: N-Fmoc-3-iodo-L-alanine tert-butyl ester
• CAS No.: 282734-33-2
• Molecular Formula: C22H24INO4
• Molecular Weight: 493.341
• DSSTox Substance ID: DTXSID10459308
• Mol file: 282734-33-2.mol

Synonyms:282734-33-2;N-FMOC-3-IODO-L-ALANINE TERT-BUTYL ESTER;(R)-tert-Butyl 2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-iodopropanoate;tert-butyl (2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-iodopropanoate;(R)-2-(9H-FLUOREN-9-YLMETHOXYCARBONYLAMINO)-3-IODO-PROPIONIC ACID TERT-BUTYL ESTER;DTXSID10459308;MFCD11053633;AS-37754;CS-0171837;A923997;J-017026;tert-Butyl (2R)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-iodopropionate;tert-Butyl(R)-2-((((9h-fluoren-9-yl)methoxy)carbonyl)amino)-3-iodopropanoate

Chemical Property of N-Fmoc-3-iodo-L-alanine tert-butyl ester

Chemical Property:

• PSA: 64.63000
• LogP: 5.06130
• Storage Temp.: 2-8°C(protect from light)
• XLogP3: 5.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 8
• Exact Mass: 493.07501
• Heavy Atom Count: 28
• Complexity: 539

Purity/Quality:

97% ^*data from raw suppliers

(R)-2-(9H-FLUOREN-9-YLMETHOXYCARBONYLAMINO)-3-IODO-PROPIONIC ACID TERT-BUTYL ESTER 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of N-Fmoc-3-iodo-L-alanine tert-butyl ester

There total 2 articles about N-Fmoc-3-iodo-L-alanine tert-butyl 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-(9H-fluoren-9-ylmethoxycarbonyl)-L-serine (73724-45-5) → (2R)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-iodopropionic acid tert-butyl ester (282734-33-2)

Guidance literature:

Multi-step reaction with 2 steps

1: dichloromethane; cyclohexane

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

With 1H-imidazole; iodine; triphenylphosphine; In dichloromethane; cyclohexane;

DOI:10.1080/10426507.2019.1603721

Reference yield:

N-(9H-fluoren-9-ylmethoxycarbonyl)-L-serine (73724-45-5) → (2R)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-iodopropionic acid tert-butyl ester (282734-33-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: dicyclohexylcarbodiimide; copper(I) chloride / 72 h / 20 °C

1.2: 67 percent / CH₂Cl₂ / 2 h / 20 °C

2.1: 88 percent / methyltriphenoxyphosphonium iodide / dimethylformamide / 1 h / 20 °C

With methyltriphenoxyphosphonium iodide; dicyclohexyl-carbodiimide; copper(l) chloride; In N,N-dimethyl-formamide;

DOI:10.1021/jm050958a

Reference yield: 91.0%

5-bromo-1-(p-tolylsulfonyl)pyrrolo[2,3-b]pyridine (479552-71-1) + (2R)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-iodopropionic acid tert-butyl ester (282734-33-2) → tert-butyl (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)propanoate

Guidance literature:

(2R)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-iodopropionic acid tert-butyl ester; With iodine; zinc; In N,N-dimethyl-formamide; at 20 ℃; for 0.583333h;

5-bromo-1-(p-tolylsulfonyl)pyrrolo[2,3-b]pyridine; With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; XPhos; In N,N-dimethyl-formamide; at 55 ℃; for 3h;

DOI:10.1021/acs.joc.0c00973

upstream raw materials:

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

Downstream raw materials:

(2S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)propionic acid tert-butyl ester

(2S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-(4-nitrophenyl)propionic acid tert-butyl ester

(2S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-(2',3',4'-trimethoxyphenyl)propionic acid tert-butyl ester

(2S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-(3',4',5'-trimethoxyphenyl)propionic acid tert-butyl ester