(2S,3R)-2-{(R)-2-(4-Benzyloxy-phenyl)-2-[(R)-2-tert-butoxycarbonylamino-2-(3,5-dibromo-4-hydroxy-phenyl)-acetylamino]-acetylamino}-3-(3,5-dichloro-4-hydroxy-phenyl)-3-hydroxy-propionic acid methyl ester

Base Information

• Chemical Name: (2S,3R)-2-{(R)-2-(4-Benzyloxy-phenyl)-2-[(R)-2-tert-butoxycarbonylamino-2-(3,5-dibromo-4-hydroxy-phenyl)-acetylamino]-acetylamino}-3-(3,5-dichloro-4-hydroxy-phenyl)-3-hydroxy-propionic acid methyl ester
• CAS No.: 123593-49-7
• Molecular Formula: C₃₈H₃₇Br₂Cl₂N₃O₁₀
• Molecular Weight: 926.44
• Mol file: 123593-49-7.mol

Synonyms:(2S,3R)-2-{(R)-2-(4-Benzyloxy-phenyl)-2-[(R)-2-tert-butoxycarbonylamino-2-(3,5-dibromo-4-hydroxy-phenyl)-acetylamino]-acetylamino}-3-(3,5-dichloro-4-hydroxy-phenyl)-3-hydroxy-propionic acid methyl ester

Chemical Property of (2S,3R)-2-{(R)-2-(4-Benzyloxy-phenyl)-2-[(R)-2-tert-butoxycarbonylamino-2-(3,5-dibromo-4-hydroxy-phenyl)-acetylamino]-acetylamino}-3-(3,5-dichloro-4-hydroxy-phenyl)-3-hydroxy-propionic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R)-2-{(R)-2-(4-Benzyloxy-phenyl)-2-[(R)-2-tert-butoxycarbonylamino-2-(3,5-dibromo-4-hydroxy-phenyl)-acetylamino]-acetylamino}-3-(3,5-dichloro-4-hydroxy-phenyl)-3-hydroxy-propionic acid methyl ester

There total 7 articles about (2S,3R)-2-{(R)-2-(4-Benzyloxy-phenyl)-2-[(R)-2-tert-butoxycarbonylamino-2-(3,5-dibromo-4-hydroxy-phenyl)-acetylamino]-acetylamino}-3-(3,5-dichloro-4-hydroxy-phenyl)-3-hydroxy-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: 93.0%

(2S,3R)-3-(4-Allyloxy-3,5-dichloro-phenyl)-2-{(R)-2-(4-benzyloxy-phenyl)-2-[(R)-2-tert-butoxycarbonylamino-2-(3,5-dibromo-4-hydroxy-phenyl)-acetylamino]-acetylamino}-3-hydroxy-propionic acid methyl ester (123593-48-6) → (2S,3R)-2-{(R)-2-(4-Benzyloxy-phenyl)-2-[(R)-2-tert-butoxycarbonylamino-2-(3,5-dibromo-4-hydroxy-phenyl)-acetylamino]-acetylamino}-3-(3,5-dichloro-4-hydroxy-phenyl)-3-hydroxy-propionic acid methyl ester (123593-49-7)

Guidance literature:

With tri-n-butyl-tin hydride; bis-triphenylphosphine-palladium(II) chloride;

DOI:10.1021/ja00206a021

Reference yield:

D-4-hydroxyphenylglycine (22818-40-2) → (2S,3R)-2-{(R)-2-(4-Benzyloxy-phenyl)-2-[(R)-2-tert-butoxycarbonylamino-2-(3,5-dibromo-4-hydroxy-phenyl)-acetylamino]-acetylamino}-3-(3,5-dichloro-4-hydroxy-phenyl)-3-hydroxy-propionic acid methyl ester (123593-49-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) Br₂ / 1.) acetic acid, 2.) aq. dioxane

2: 1.) trifluoroacetic acid, thioanisole, 2.) 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride (EDC), hydroxybenzotriazole (HOBt)

3: 93 percent / Bu₃SnH / Pd(PPh₃)2Cl₂

With methyl-phenyl-thioether; bromine; tri-n-butyl-tin hydride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; bis-triphenylphosphine-palladium(II) chloride;

DOI:10.1021/ja00206a021

Reference yield:

(R)-(4-benzyloxyphenyl)(tert-butoxycarbonylamino)acetic acid (127526-64-1) → (2S,3R)-2-{(R)-2-(4-Benzyloxy-phenyl)-2-[(R)-2-tert-butoxycarbonylamino-2-(3,5-dibromo-4-hydroxy-phenyl)-acetylamino]-acetylamino}-3-(3,5-dichloro-4-hydroxy-phenyl)-3-hydroxy-propionic acid methyl ester (123593-49-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) trifluoroacetic acid, thioanisole, 2.) diisopropylcarbodiimide, hydroxybenzotriazole

2: 1.) trifluoroacetic acid, thioanisole, 2.) 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride (EDC), hydroxybenzotriazole (HOBt)

3: 93 percent / Bu₃SnH / Pd(PPh₃)2Cl₂

With methyl-phenyl-thioether; tri-n-butyl-tin hydride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; diisopropyl-carbodiimide; bis-triphenylphosphine-palladium(II) chloride;

DOI:10.1021/ja00206a021

upstream raw materials:

(2S,3R)-3-(4-Allyloxy-3,5-dichloro-phenyl)-2-{(R)-2-(4-benzyloxy-phenyl)-2-[(R)-2-tert-butoxycarbonylamino-2-(3,5-dibromo-4-hydroxy-phenyl)-acetylamino]-acetylamino}-3-hydroxy-propionic acid methyl ester

D-4-hydroxyphenylglycine

(R)-(4-benzyloxyphenyl)(tert-butoxycarbonylamino)acetic acid

tert-Butyl pyrocarbonate

Downstream raw materials:

(8R,11R,14S,15R)-11-(4-Benzyloxy-phenyl)-5-bromo-8-tert-butoxycarbonylamino-18,19-dichloro-15-hydroxy-7-methoxy-4,9,12-trioxo-2-oxa-10,13-diaza-tricyclo[14.2.2.1^3,7]henicosa-1⁽¹⁹⁾,3⁽²¹⁾,5,16⁽²⁰⁾,17-pentaene-14-carboxylic acid methyl ester

C₅₈H₅₉Cl₄N₇O₁₅

(8R,11R,14S,15R)-11-(4-Benzyloxy-phenyl)-5-bromo-8-tert-butoxycarbonylamino-18,19-dichloro-4,15-dihydroxy-9,12-dioxo-2-oxa-10,13-diaza-tricyclo[14.2.2.1^3,7]henicosa-1⁽¹⁹⁾,3⁽²¹⁾,4,6,16⁽²⁰⁾,17-hexaene-14-carboxylic acid methyl ester

C₆₁H₆₄BrCl₄N₇O₁₅