3-Iodo-L-tyrosine methyl ester

Base Information

• Chemical Name: 3-Iodo-L-tyrosine methyl ester
• CAS No.: 70277-02-0
• Molecular Formula: C10H12 I N O3
• Molecular Weight: 321.115
• Hs Code.: 2922509090
• DSSTox Substance ID: DTXSID50459640
• Nikkaji Number: J1.617.495E
• Wikidata: Q72484787
• Mol file: 70277-02-0.mol

Synonyms:70277-02-0;3-Iodo-L-tyrosine methyl ester;(S)-Methyl 2-amino-3-(4-hydroxy-3-iodophenyl)propanoate;methyl (2S)-2-amino-3-(4-hydroxy-3-iodophenyl)propanoate;methyl (S)-2-amino-3-(4-hydroxy-3-iodophenyl)propanoate;C10H12INO3;L-Tyrosine, 3-iodo-, methyl ester;3-Iodotyrosine methyl ester;3-iodo-tyrosine methyl ester;SCHEMBL951158;DTXSID50459640;VCA27702;MFCD07778602;AKOS015889930;AC-4633;BS-24433;EN300-7392588;(S)-Methyl 2-amino-3-(4-hydroxy-3-iodophenyl)propanoate (H-L-Tyr(3-I)-OMe)

Chemical Property of 3-Iodo-L-tyrosine methyl ester

Chemical Property:

• Vapor Pressure: 2.65E-05mmHg at 25°C
• Boiling Point: 347.6oC at 760 mmHg
• Flash Point: 164oC
• PSA: 72.55000
• Density: 1.751g/cm3
• LogP: 1.73990
• Storage Temp.: 2-8°C(protect from light)
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 320.98619
• Heavy Atom Count: 15
• Complexity: 225

Purity/Quality:

99% ^*data from raw suppliers

(S)-Methyl 2-amino-3-(4-hydroxy-3-iodophenyl)propanoate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C(CC1=CC(=C(C=C1)O)I)N
• Isomeric SMILES: COC(=O)[C@H](CC1=CC(=C(C=C1)O)I)N

Technology Process of 3-Iodo-L-tyrosine methyl ester

There total 2 articles about 3-Iodo-L-tyrosine 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%

methanol (67-56-1) + 3-Iodo-L-tyrosine (70-78-0) → 3-iodo-L-tyrosine methyl ester (70277-02-0)

Guidance literature:

With thionyl chloride; at 0 ℃; for 12h; Inert atmosphere;

DOI:10.5935/0103-5053.20150038

Reference yield: 78.0%

L-Tyr-OMe (1080-06-4) → 3-iodo-L-tyrosine methyl ester (70277-02-0)

Guidance literature:

With chloroamine-T; sodium iodide; In water; for 0.333333h;

DOI:10.1002/(SICI)1099-1344(199804)41:4<255::AID-JLCR89>3.3.CO;2-F

Reference yield: 90.0%

di-tert-butyl dicarbonate (24424-99-5) + 3-iodo-L-tyrosine methyl ester (70277-02-0) → methyl (S)-2-((tert-butoxycarbonyl)amino)-3-(4-hydroxy-3-iodophenyl)propanoate (119336-08-2,79677-59-1)

Guidance literature:

With sodium hydrogencarbonate; In methanol; at 20 ℃; for 15h; Inert atmosphere;

DOI:10.5935/0103-5053.20150038

upstream raw materials:

methanol

3-Iodo-L-tyrosine

L-Tyr-OMe

Downstream raw materials:

(2S,3R)-2-[3-(4-Benzyloxy-phenyl)-propyl]-3-[(S)-2-(4-hydroxy-3-iodo-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-5-methyl-hexanoic acid tert-butyl ester

(S)-N-benzyloxycarbonyl-3-(4-hydroxy-3-iodophenyl)alanine methyl ester

methyl (S)-2-((tert-butoxycarbonyl)amino)-3-(4-hydroxy-3-iodophenyl)propanoate

2-tert-butoxycarbonylamino-3-(4-methoxy-3-vinyl-phenyl)-propionic acid methyl ester

Refernces

• 1、 Vasconcelos, Stanley N.S.,Barbeiro, Cristiane S.,Khan, Amna N.,Stefani, Hélio A.. "Synthesis of biphenyl tyrosine via cross-coupling Suzuki-Miyaura reaction using aryltrifluoroborate salts". . p. 765 - 774. Retrieved 2015/04/14.
• 2、 Liu, Jian,Luo, Chuanyun,Smith, Peter A.,Chin, Jodie K.,Page, Malcolm G. P.,Paetzel, Mark,Romesberg, Floyd E.. "Synthesis and characterization of the arylomycin lipoglycopeptide antibiotics and the crystallographic analysis of their complex with signal peptidase". supporting information; experimental part. p. 17869 - 17877. Retrieved 2012/01/05.