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

Base Information

• Chemical Name: Acetic acid (R)-3-{3-[4-((S)-3-acetoxy-2-acetylamino-propyl)-phenoxy]-4-methoxy-phenyl}-2-((R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionylamino)-propyl ester
• CAS No.: 143817-67-8
• Molecular Formula: C₃₅H₃₉F₃N₂O₉
• Molecular Weight: 688.698

Synonyms:

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

There total 24 articles about Acetic acid (R)-3-{3-[4-((S)-3-acetoxy-2-acetylamino-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-acetylamino-propyl)-phenoxy]-4-methoxy-phenyl}-2-((R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionylamino)-propyl ester (143817-67-8,143899-98-3)

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: 68 percent / methanol, p-toluenesulfonic acid / Ambient temperature

8: 100 percent / Et₃N, DMAP / CH₂Cl₂

9: 93 percent / NaBH₄ / methanol

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

11: 100 percent / n-Bu₄NF / tetrahydrofuran

With methanol; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; Tebbe's reagent; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; toluene-4-sulfonic acid; di(1H-imidazol-2-yl)methanethione; triethylamine; dicyclohexyl-carbodiimide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetone; toluene;

DOI:10.1021/jo00048a005

Reference yield:

Boc-Tyr-OH (3978-80-1) → Acetic acid (R)-3-{3-[4-((S)-3-acetoxy-2-acetylamino-propyl)-phenoxy]-4-methoxy-phenyl}-2-((R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionylamino)-propyl ester (143817-67-8,143899-98-3)

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: toluene / 120 °C

6: DDQ

7: methanol, p-toluenesulfonic acid / Ambient temperature

8: Et₃N, DMAP / CH₂Cl₂

9: NaBH₄ / methanol

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

11: n-Bu₄NF / tetrahydrofuran

With methanol; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; Tebbe's reagent; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; toluene-4-sulfonic acid; di(1H-imidazol-2-yl)methanethione; triethylamine; dicyclohexyl-carbodiimide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; 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-acetylamino-propyl)-phenoxy]-4-methoxy-phenyl}-2-((R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionylamino)-propyl ester (143817-67-8,143899-98-3)

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: 68 percent / methanol, p-toluenesulfonic acid / Ambient temperature

7: 100 percent / Et₃N, DMAP / CH₂Cl₂

8: 93 percent / NaBH₄ / methanol

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

10: 100 percent / n-Bu₄NF / tetrahydrofuran

With methanol; dmap; sodium tetrahydroborate; Tebbe's reagent; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; toluene-4-sulfonic acid; di(1H-imidazol-2-yl)methanethione; triethylamine; dicyclohexyl-carbodiimide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; dichloromethane; acetone; toluene;

DOI:10.1021/jo00048a005

upstream raw materials:

R-(+)-α-trifluoromethyl-α-methoxy-phenylacetic acid

acetic anhydride

(S)-4-{3-[4-((S)-2-tert-Butoxycarbonylamino-3-hydroxy-propyl)-phenoxy]-4-methoxy-benzyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

Boc-Tyr-OH

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