(S)-2-[(R)-2-[(R)-2-Benzyloxycarbonylamino-2-(4-hydroxy-3,5-diiodo-phenyl)-acetylamino]-2-(3,5-dichloro-4-hydroxy-phenyl)-acetylamino]-3-(3,5-dibromo-4-hydroxy-phenyl)-propionic acid methyl ester

Base Information

• Chemical Name: (S)-2-[(R)-2-[(R)-2-Benzyloxycarbonylamino-2-(4-hydroxy-3,5-diiodo-phenyl)-acetylamino]-2-(3,5-dichloro-4-hydroxy-phenyl)-acetylamino]-3-(3,5-dibromo-4-hydroxy-phenyl)-propionic acid methyl ester
• CAS No.: 246512-37-8
• Molecular Formula: C₃₄H₂₇Br₂Cl₂I₂N₃O₉
• Molecular Weight: 1106.13

Synonyms:(S)-2-[(R)-2-[(R)-2-Benzyloxycarbonylamino-2-(4-hydroxy-3,5-diiodo-phenyl)-acetylamino]-2-(3,5-dichloro-4-hydroxy-phenyl)-acetylamino]-3-(3,5-dibromo-4-hydroxy-phenyl)-propionic acid methyl ester

Chemical Property of (S)-2-[(R)-2-[(R)-2-Benzyloxycarbonylamino-2-(4-hydroxy-3,5-diiodo-phenyl)-acetylamino]-2-(3,5-dichloro-4-hydroxy-phenyl)-acetylamino]-3-(3,5-dibromo-4-hydroxy-phenyl)-propionic acid methyl ester

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Technology Process of (S)-2-[(R)-2-[(R)-2-Benzyloxycarbonylamino-2-(4-hydroxy-3,5-diiodo-phenyl)-acetylamino]-2-(3,5-dichloro-4-hydroxy-phenyl)-acetylamino]-3-(3,5-dibromo-4-hydroxy-phenyl)-propionic acid methyl ester

There total 4 articles about (S)-2-[(R)-2-[(R)-2-Benzyloxycarbonylamino-2-(4-hydroxy-3,5-diiodo-phenyl)-acetylamino]-2-(3,5-dichloro-4-hydroxy-phenyl)-acetylamino]-3-(3,5-dibromo-4-hydroxy-phenyl)-propionic acid 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: 46.0%

(R)-Benzyloxycarbonylamino-(4-hydroxy-3,5-diiodo-phenyl)-acetic acid (246512-33-4) + (S)-2-[(R)-2-tert-Butoxycarbonylamino-2-(3,5-dichloro-4-hydroxy-phenyl)-acetylamino]-3-(3,5-dibromo-4-hydroxy-phenyl)-propionic acid methyl ester → (S)-2-[(R)-2-[(R)-2-Benzyloxycarbonylamino-2-(4-hydroxy-3,5-diiodo-phenyl)-acetylamino]-2-(3,5-dichloro-4-hydroxy-phenyl)-acetylamino]-3-(3,5-dibromo-4-hydroxy-phenyl)-propionic acid methyl ester (246512-37-8)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4039(99)01283-6

Reference yield:

3',5'-dibromo-L-tyrosine methyl ester (67470-21-7,173383-29-4) → (S)-2-[(R)-2-[(R)-2-Benzyloxycarbonylamino-2-(4-hydroxy-3,5-diiodo-phenyl)-acetylamino]-2-(3,5-dichloro-4-hydroxy-phenyl)-acetylamino]-3-(3,5-dibromo-4-hydroxy-phenyl)-propionic acid methyl ester (246512-37-8)

Guidance literature:

Multi-step reaction with 2 steps

1: BOP-Cl / tetrahydrofuran

2: 46 percent / EDCI; HOBt / tetrahydrofuran; CH₂Cl₂

With bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; dichloromethane; 1: Acylation / 2: Acylation;

DOI:10.1016/S0040-4039(99)01283-6

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → (S)-2-[(R)-2-[(R)-2-Benzyloxycarbonylamino-2-(4-hydroxy-3,5-diiodo-phenyl)-acetylamino]-2-(3,5-dichloro-4-hydroxy-phenyl)-acetylamino]-3-(3,5-dibromo-4-hydroxy-phenyl)-propionic acid methyl ester (246512-37-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 51 percent

2: 46 percent / EDCI; HOBt / tetrahydrofuran; CH₂Cl₂

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; dichloromethane; 2: Acylation;

DOI:10.1016/S0040-4039(99)01283-6

upstream raw materials:

(R)-Benzyloxycarbonylamino-(4-hydroxy-3,5-diiodo-phenyl)-acetic acid

3',5'-dibromo-L-tyrosine methyl ester

benzyl chloroformate

(R)-2-((tert-butoxycarbonyl)amino)-2-(3,5-dichloro-4-hydroxyphenyl)acetic acid

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