4-(1-benzyloxycarbonyl-2-phenyl-ethylcarbamoyl)-4-{2-[(2-{2-[2-tert-butoxycarbonylamino-3-(trityl-carbamoyl)-propionylamino]-1-hydroxy-4-methyl-pentyl}-cyclopentanecarbonyl)-amino]-propionylamino}-butyric acid benzyl ester

Base Information

• Chemical Name: 4-(1-benzyloxycarbonyl-2-phenyl-ethylcarbamoyl)-4-{2-[(2-{2-[2-tert-butoxycarbonylamino-3-(trityl-carbamoyl)-propionylamino]-1-hydroxy-4-methyl-pentyl}-cyclopentanecarbonyl)-amino]-propionylamino}-butyric acid benzyl ester
• CAS No.: 864238-56-2
• Molecular Formula: C₇₁H₈₄N₆O₁₂
• Molecular Weight: 1213.48
• Mol file: 864238-56-2.mol

Synonyms:4-(1-benzyloxycarbonyl-2-phenyl-ethylcarbamoyl)-4-{2-[(2-{2-[2-tert-butoxycarbonylamino-3-(trityl-carbamoyl)-propionylamino]-1-hydroxy-4-methyl-pentyl}-cyclopentanecarbonyl)-amino]-propionylamino}-butyric acid benzyl ester

Chemical Property of 4-(1-benzyloxycarbonyl-2-phenyl-ethylcarbamoyl)-4-{2-[(2-{2-[2-tert-butoxycarbonylamino-3-(trityl-carbamoyl)-propionylamino]-1-hydroxy-4-methyl-pentyl}-cyclopentanecarbonyl)-amino]-propionylamino}-butyric acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-(1-benzyloxycarbonyl-2-phenyl-ethylcarbamoyl)-4-{2-[(2-{2-[2-tert-butoxycarbonylamino-3-(trityl-carbamoyl)-propionylamino]-1-hydroxy-4-methyl-pentyl}-cyclopentanecarbonyl)-amino]-propionylamino}-butyric acid benzyl ester

There total 11 articles about 4-(1-benzyloxycarbonyl-2-phenyl-ethylcarbamoyl)-4-{2-[(2-{2-[2-tert-butoxycarbonylamino-3-(trityl-carbamoyl)-propionylamino]-1-hydroxy-4-methyl-pentyl}-cyclopentanecarbonyl)-amino]-propionylamino}-butyric acid benzyl 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:

(4S,5S)-isobutyl-5-methoxycarbonylethynyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (864238-48-2) → 4-(1-benzyloxycarbonyl-2-phenyl-ethylcarbamoyl)-4-{2-[(2-{2-[2-tert-butoxycarbonylamino-3-(trityl-carbamoyl)-propionylamino]-1-hydroxy-4-methyl-pentyl}-cyclopentanecarbonyl)-amino]-propionylamino}-butyric acid benzyl ester (864238-56-2)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 90 percent / quinoline; H₂ / Lindlar catalyst / benzene / 20 °C

2.1: triisopropyl phosphite; palladium acetate / toluene / 16 h / 100 °C

2.2: 0.85 g / NaOMe / methanol / 6 h / Heating

3.1: 90 percent / aq. NaIO₄; OsO₄ / tetrahydrofuran / 14 h / 20 °C

4.1: 99 percent / Na₂SO₄ / methanol / 2 h / Heating

5.1: catecholborane / CHCl₃; tetrahydrofuran / 0 - 20 °C

5.2: 68 percent / NaOAc*3H₂O / CHCl₃; tetrahydrofuran / 3 h / Heating

6.1: aq. KOH / methanol / 3 h / 65 °C

7.1: 100 mg / PyBOP; i-Pr₂NEt / CH₂Cl₂ / 4 h / 0 °C

8.1: TFA / CH₂Cl₂ / 1 h / 20 °C

9.1: 80 mg / PyBOP; i-Pr₂NEt / CH₂Cl₂ / 20 °C

With quinoline; potassium hydroxide; sodium periodate; osmium(VIII) oxide; triisopropyl phosphite; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; hydrogen; palladium diacetate; sodium sulfate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; benzo[1,3,2]dioxaborole; Lindlar's catalyst; In tetrahydrofuran; methanol; dichloromethane; chloroform; toluene; benzene; 1.1: Lindlar reduction;

DOI:10.1021/jm050142+

Reference yield:

(S)-4-((S)-2-{[(1R,2R)-2-((1S,2S)-2-Amino-1-hydroxy-4-methyl-pentyl)-cyclopentanecarbonyl]-amino}-propionylamino)-4-((S)-1-benzyloxycarbonyl-2-phenyl-ethylcarbamoyl)-butyric acid benzyl ester + Nα-tert-butoxycarbonyl-Nω-triphenylmethyl-L-asparagine (132388-68-2) → 4-(1-benzyloxycarbonyl-2-phenyl-ethylcarbamoyl)-4-{2-[(2-{2-[2-tert-butoxycarbonylamino-3-(trityl-carbamoyl)-propionylamino]-1-hydroxy-4-methyl-pentyl}-cyclopentanecarbonyl)-amino]-propionylamino}-butyric acid benzyl ester (864238-56-2)

Guidance literature:

With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃;

DOI:10.1021/jm050142+

Reference yield:

(4S)-isobutyl-(5S)-(2-methoxycarbonyl-vinyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (864238-49-3) → 4-(1-benzyloxycarbonyl-2-phenyl-ethylcarbamoyl)-4-{2-[(2-{2-[2-tert-butoxycarbonylamino-3-(trityl-carbamoyl)-propionylamino]-1-hydroxy-4-methyl-pentyl}-cyclopentanecarbonyl)-amino]-propionylamino}-butyric acid benzyl ester (864238-56-2)

Guidance literature:

Multi-step reaction with 8 steps

1.1: triisopropyl phosphite; palladium acetate / toluene / 16 h / 100 °C

1.2: 0.85 g / NaOMe / methanol / 6 h / Heating

2.1: 90 percent / aq. NaIO₄; OsO₄ / tetrahydrofuran / 14 h / 20 °C

3.1: 99 percent / Na₂SO₄ / methanol / 2 h / Heating

4.1: catecholborane / CHCl₃; tetrahydrofuran / 0 - 20 °C

4.2: 68 percent / NaOAc*3H₂O / CHCl₃; tetrahydrofuran / 3 h / Heating

5.1: aq. KOH / methanol / 3 h / 65 °C

6.1: 100 mg / PyBOP; i-Pr₂NEt / CH₂Cl₂ / 4 h / 0 °C

7.1: TFA / CH₂Cl₂ / 1 h / 20 °C

8.1: 80 mg / PyBOP; i-Pr₂NEt / CH₂Cl₂ / 20 °C

With potassium hydroxide; sodium periodate; osmium(VIII) oxide; triisopropyl phosphite; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; palladium diacetate; sodium sulfate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; benzo[1,3,2]dioxaborole; In tetrahydrofuran; methanol; dichloromethane; chloroform; toluene;

DOI:10.1021/jm050142+

upstream raw materials:

N^α-tert-butoxycarbonyl-N^ω-triphenylmethyl-L-asparagine

(4S)-isobutyl-(5S)-(2-methoxycarbonyl-vinyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

(4S,5S)-isobutyl-5-methoxycarbonylethynyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

(4S)-isobutyl-(5S)-((2R)-methoxycarbonyl-cyclopentyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Downstream raw materials:

4-(1-benzyloxycarbonyl-2-phenyl-ethylcarbamoyl)-4-{2-[(2-{2-[2-(2-tert-butoxycarbonylamino-3-methyl-butyrylamino)-3-(trityl-carbamoyl)-propionylamino]-1-hydroxy-4-methyl-pentyl}-cyclopentanecarbonyl)-amino]-propionylamino}-butyric acid benzyl ester