Acetic acid (S)-3-{3-[4-((S)-3-acetoxy-2-tert-butoxycarbonylamino-propyl)-phenoxy]-4-methoxy-phenyl}-2-((R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionylamino)-propyl ester

Base Information

• Chemical Name: Acetic acid (S)-3-{3-[4-((S)-3-acetoxy-2-tert-butoxycarbonylamino-propyl)-phenoxy]-4-methoxy-phenyl}-2-((R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionylamino)-propyl ester
• CAS No.: 143817-68-9
• Molecular Formula: C₃₈H₄₅F₃N₂O₁₀
• Molecular Weight: 746.778

Synonyms:

Chemical Property of Acetic acid (S)-3-{3-[4-((S)-3-acetoxy-2-tert-butoxycarbonylamino-propyl)-phenoxy]-4-methoxy-phenyl}-2-((R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionylamino)-propyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (S)-3-{3-[4-((S)-3-acetoxy-2-tert-butoxycarbonylamino-propyl)-phenoxy]-4-methoxy-phenyl}-2-((R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionylamino)-propyl ester

There total 12 articles about Acetic acid (S)-3-{3-[4-((S)-3-acetoxy-2-tert-butoxycarbonylamino-propyl)-phenoxy]-4-methoxy-phenyl}-2-((R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionylamino)-propyl 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:

Boc-Tyr-OH (3978-80-1) → Acetic acid (S)-3-{3-[4-((S)-3-acetoxy-2-tert-butoxycarbonylamino-propyl)-phenoxy]-4-methoxy-phenyl}-2-((R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionylamino)-propyl ester (143817-68-9)

Guidance literature:

Multi-step reaction with 12 steps

1: 82 percent / LiAlH₄ / diethyl ether

2: 87 percent / p-toluenesulfonic acid / acetone

3: 82 percent / DCC, DMAP

4: 64 percent / Tebbe's reagent / toluene

5: 46 percent / toluene / 120 °C

6: DDQ

7: NaBH₄ / methanol

8: 1.) thiocarbonyl diimidazole, DMAP, 2.) n-Bu₃SnH, AIBN / 2.) toluene

9: methanol, p-toluenesulfonic acid

10: hydrogen / Pd(OH)2

11: Et₃N, HOBt, EDCI

12: DMAP / CH₂Cl₂

With methanol; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; Tebbe's reagent; 2,2'-azobis(isobutyronitrile); hydrogen; tri-n-butyl-tin hydride; benzotriazol-1-ol; toluene-4-sulfonic acid; di(1H-imidazol-2-yl)methanethione; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; dicyclohexyl-carbodiimide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium dihydroxide; In methanol; diethyl ether; dichloromethane; acetone; toluene;

DOI:10.1021/jo00048a005

Reference yield:

N-(tert-butyloxycarbonyl)-L-tyrosinol (83345-46-4,282100-80-5) → Acetic acid (S)-3-{3-[4-((S)-3-acetoxy-2-tert-butoxycarbonylamino-propyl)-phenoxy]-4-methoxy-phenyl}-2-((R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionylamino)-propyl ester (143817-68-9)

Guidance literature:

Multi-step reaction with 11 steps

1: 87 percent / p-toluenesulfonic acid / acetone

2: 82 percent / DCC, DMAP

3: 64 percent / Tebbe's reagent / toluene

4: 46 percent / toluene / 120 °C

5: DDQ

6: NaBH₄ / methanol

7: 1.) thiocarbonyl diimidazole, DMAP, 2.) n-Bu₃SnH, AIBN / 2.) toluene

8: methanol, p-toluenesulfonic acid

9: hydrogen / Pd(OH)2

10: Et₃N, HOBt, EDCI

11: DMAP / CH₂Cl₂

With methanol; dmap; sodium tetrahydroborate; Tebbe's reagent; 2,2'-azobis(isobutyronitrile); hydrogen; tri-n-butyl-tin hydride; benzotriazol-1-ol; toluene-4-sulfonic acid; di(1H-imidazol-2-yl)methanethione; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; dicyclohexyl-carbodiimide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium dihydroxide; In methanol; dichloromethane; acetone; toluene;

DOI:10.1021/jo00048a005

Reference yield:

N-(tert-butoxycarbonyl)-2,2-dimethyl-4-(4-hydroxyphenyl)-1,3-oxazolidine (143817-58-7) → Acetic acid (S)-3-{3-[4-((S)-3-acetoxy-2-tert-butoxycarbonylamino-propyl)-phenoxy]-4-methoxy-phenyl}-2-((R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionylamino)-propyl ester (143817-68-9)

Guidance literature:

Multi-step reaction with 10 steps

1: 82 percent / DCC, DMAP

2: 64 percent / Tebbe's reagent / toluene

3: 46 percent / toluene / 120 °C

4: DDQ

5: NaBH₄ / methanol

6: 1.) thiocarbonyl diimidazole, DMAP, 2.) n-Bu₃SnH, AIBN / 2.) toluene

7: methanol, p-toluenesulfonic acid

8: hydrogen / Pd(OH)2

9: Et₃N, HOBt, EDCI

10: DMAP / CH₂Cl₂

With methanol; dmap; sodium tetrahydroborate; Tebbe's reagent; 2,2'-azobis(isobutyronitrile); hydrogen; tri-n-butyl-tin hydride; benzotriazol-1-ol; toluene-4-sulfonic acid; di(1H-imidazol-2-yl)methanethione; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; dicyclohexyl-carbodiimide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium dihydroxide; In methanol; dichloromethane; toluene;

DOI:10.1021/jo00048a005

upstream raw materials:

acetic anhydride

[(S)-1-Hydroxymethyl-2-(4-{5-[(S)-3-hydroxy-2-((R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionylamino)-propyl]-2-methoxy-phenoxy}-phenyl)-ethyl]-carbamic acid tert-butyl ester

Boc-Tyr-OH

N-(tert-butyloxycarbonyl)-L-tyrosinol

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