N-tert-butoxycarbonyl-L-3-iodotyrosyl-L-3-iodotyrosine methyl ester

Base Information

• Chemical Name: N-tert-butoxycarbonyl-L-3-iodotyrosyl-L-3-iodotyrosine methyl ester
• CAS No.: 1373311-90-0
• Molecular Formula: C₂₄H₂₈I₂N₂O₇
• Molecular Weight: 710.305
• Mol file: 1373311-90-0.mol

Synonyms:N-tert-butoxycarbonyl-L-3-iodotyrosyl-L-3-iodotyrosine methyl ester

Chemical Property of N-tert-butoxycarbonyl-L-3-iodotyrosyl-L-3-iodotyrosine methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-tert-butoxycarbonyl-L-3-iodotyrosyl-L-3-iodotyrosine methyl ester

There total 4 articles about N-tert-butoxycarbonyl-L-3-iodotyrosyl-L-3-iodotyrosine 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: 90.0%

2-amino-3-(3-iodo-4-hydroxyphenyl)propionic acid methyl ester hydrochloride (79677-58-0,122908-62-7) + N-tert-butyloxycarbonyl-3-iodo-L-tyrosine (71400-63-0,478183-68-5) → N-tert-butoxycarbonyl-L-3-iodotyrosyl-L-3-iodotyrosine methyl ester (1373311-90-0)

Guidance literature:

With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; In N,N-dimethyl-formamide; acetonitrile; at 0 - 20 ℃; for 16h;

DOI:10.1021/acs.jmedchem.9b01199

Reference yield: 48.0%

3-iodo-L-tyrosine methyl ester (70277-02-0) + N-tert-butyloxycarbonyl-3-iodo-L-tyrosine (71400-63-0,478183-68-5) → N-tert-butoxycarbonyl-L-3-iodotyrosyl-L-3-iodotyrosine methyl ester (1373311-90-0)

Guidance literature:

N-tert-butyloxycarbonyl-3-iodo-L-tyrosine; With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 0 ℃; for 1h;

3-iodo-L-tyrosine methyl ester; With triethylamine; In dichloromethane; N,N-dimethyl-formamide; at 20 ℃; for 15h;

DOI:10.1016/j.ejmech.2016.02.062

Reference yield:

L-tyrosine (60-18-4,18875-48-4,25619-78-7,30704-25-7) → N-tert-butoxycarbonyl-L-3-iodotyrosyl-L-3-iodotyrosine methyl ester (1373311-90-0)

Guidance literature:

Multi-step reaction with 3 steps

1: ammonium hydroxide; iodine / ethanol / 3 h / 0 °C

2: thionyl chloride / 16 h / Reflux

3: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 16 h / Inert atmosphere

With ammonium hydroxide; thionyl chloride; iodine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; In ethanol; N,N-dimethyl-formamide;

DOI:10.1021/ol300831t

upstream raw materials:

3-Iodo-L-tyrosine

L-tyrosine

2-amino-3-(3-iodo-4-hydroxyphenyl)propionic acid methyl ester hydrochloride

N-tert-butyloxycarbonyl-3-iodo-L-tyrosine

Downstream raw materials:

cyclodi(L-3-iodotyrosine)

(3S,6S)-3,6-bis(4-(benzyloxy)-3-iodobenzyl)piperazine-2,5-dione

(4²S,4⁵S)-1⁶,2⁶-bis(benzyloxy)-4(2,5)-piperazina-1,2(1,3)-dibenzenacyclopentaphane-4³,46-dione