methyl N-Cbz-3,5-dichloro-N-methyl-L-tyrosyl-3,5-dibromo-N-methyl-L-tyrosinate

Base Information

• Chemical Name: methyl N-Cbz-3,5-dichloro-N-methyl-L-tyrosyl-3,5-dibromo-N-methyl-L-tyrosinate
• CAS No.: 108969-78-4
• Molecular Formula: C₂₉H₂₈Br₂Cl₂N₂O₇
• Molecular Weight: 747.265

Synonyms:methyl N-Cbz-3,5-dichloro-N-methyl-L-tyrosyl-3,5-dibromo-N-methyl-L-tyrosinate

Chemical Property of methyl N-Cbz-3,5-dichloro-N-methyl-L-tyrosyl-3,5-dibromo-N-methyl-L-tyrosinate

Chemical Property:

Purity/Quality:

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Technology Process of methyl N-Cbz-3,5-dichloro-N-methyl-L-tyrosyl-3,5-dibromo-N-methyl-L-tyrosinate

There total 5 articles about methyl N-Cbz-3,5-dichloro-N-methyl-L-tyrosyl-3,5-dibromo-N-methyl-L-tyrosinate 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: 76.0%

2,6-dibromo-N-methyltyrosine methyl ester (108969-87-5) + N-benzyloxycarbonyl-2,6-dichloro-N-methyltyrosine (108969-88-6) → methyl N-Cbz-3,5-dichloro-N-methyl-L-tyrosyl-3,5-dibromo-N-methyl-L-tyrosinate (108969-78-4)

Guidance literature:

With dicyclohexyl-carbodiimide; In 1,4-dioxane;

DOI:10.1021/jo00389a068

Reference yield:

N-methyl-L-tyrosine (537-49-5) → methyl N-Cbz-3,5-dichloro-N-methyl-L-tyrosyl-3,5-dibromo-N-methyl-L-tyrosinate (108969-78-4)

Guidance literature:

Multi-step reaction with 3 steps

1: Br₂ / methanol / Ambient temperature

2: conc. H₂SO₄ / 46 h / Heating

3: 76 percent / N,N-dicyclohexylcarbodiimide / dioxane / 20 h / Ambient temperature

With sulfuric acid; bromine; dicyclohexyl-carbodiimide; In 1,4-dioxane; methanol;

DOI:10.1248/cpb.43.1325

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → methyl N-Cbz-3,5-dichloro-N-methyl-L-tyrosyl-3,5-dibromo-N-methyl-L-tyrosinate (108969-78-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / K₂CO₃ / acetone; H₂O / 0.5 h / Ambient temperature

2: 61 percent / Cl₂ / CHCl₃ / 1 h

3: 76 percent / N,N-dicyclohexylcarbodiimide / dioxane / 20 h / Ambient temperature

With chlorine; potassium carbonate; dicyclohexyl-carbodiimide; In 1,4-dioxane; chloroform; water; acetone;

DOI:10.1248/cpb.43.1325

upstream raw materials:

2,6-dibromo-N-methyltyrosine methyl ester

N-benzyloxycarbonyl-2,6-dichloro-N-methyltyrosine

N-methyl-L-tyrosine

benzyl chloroformate

Downstream raw materials:

(9S,12S)-12-(Benzyloxycarbonyl-methyl-amino)-5-bromo-16,17-dichloro-7-methoxy-10-methyl-4,11-dioxo-2-oxa-10-aza-tricyclo[12.2.2.1^3,7]nonadeca-1⁽¹⁷⁾,3⁽¹⁹⁾,5,14⁽¹⁸⁾,15-pentaene-9-carboxylic acid methyl ester

(9S,12S)-12-(Benzyloxycarbonyl-methyl-amino)-16,17-dichloro-5,7-dimethoxy-10-methyl-4,11-dioxo-2-oxa-10-aza-tricyclo[12.2.2.1^3,7]nonadeca-1⁽¹⁷⁾,3⁽¹⁹⁾,5,14⁽¹⁸⁾,15-pentaene-9-carboxylic acid methyl ester

deoxybouvadin

RA-VII

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