4-{1-[1-(1-{[2-(1-benzyloxycarbonyl-ethylcarbamoyl)-cyclopentyl]-hydroxy-methyl}-3-methyl-butylcarbamoyl)-2-(trityl-carbamoyl)-ethylcarbamoyl]-2-methyl-propylcarbamoyl}-4-tert-butoxycarbonylamino-butyric acid benzyl ester

Base Information

Chemical Name:4-{1-[1-(1-{[2-(1-benzyloxycarbonyl-ethylcarbamoyl)-cyclopentyl]-hydroxy-methyl}-3-methyl-butylcarbamoyl)-2-(trityl-carbamoyl)-ethylcarbamoyl]-2-methyl-propylcarbamoyl}-4-tert-butoxycarbonylamino-butyric acid benzyl ester
CAS No.:864238-64-2
Molecular Formula:C₆₇H₈₄N₆O₁₂
Molecular Weight:1165.44
Hs Code.:

4-{1-[1-(1-{[2-(1-benzyloxycarbonyl-ethylcarbamoyl)-cyclopentyl]-hydroxy-methyl}-3-methyl-butylcarbamoyl)-2-(trityl-carbamoyl)-ethylcarbamoyl]-2-methyl-propylcarbamoyl}-4-<i>tert</i>-butoxycarbonylamino-butyric acid benzyl ester

Synonyms:4-{1-[1-(1-{[2-(1-benzyloxycarbonyl-ethylcarbamoyl)-cyclopentyl]-hydroxy-methyl}-3-methyl-butylcarbamoyl)-2-(trityl-carbamoyl)-ethylcarbamoyl]-2-methyl-propylcarbamoyl}-4-tert-butoxycarbonylamino-butyric acid benzyl ester

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Chemical Property of 4-{1-[1-(1-{[2-(1-benzyloxycarbonyl-ethylcarbamoyl)-cyclopentyl]-hydroxy-methyl}-3-methyl-butylcarbamoyl)-2-(trityl-carbamoyl)-ethylcarbamoyl]-2-methyl-propylcarbamoyl}-4-tert-butoxycarbonylamino-butyric acid benzyl ester

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Technology Process of 4-{1-[1-(1-{[2-(1-benzyloxycarbonyl-ethylcarbamoyl)-cyclopentyl]-hydroxy-methyl}-3-methyl-butylcarbamoyl)-2-(trityl-carbamoyl)-ethylcarbamoyl]-2-methyl-propylcarbamoyl}-4-tert-butoxycarbonylamino-butyric acid benzyl ester

There total 13 articles about 4-{1-[1-(1-{[2-(1-benzyloxycarbonyl-ethylcarbamoyl)-cyclopentyl]-hydroxy-methyl}-3-methyl-butylcarbamoyl)-2-(trityl-carbamoyl)-ethylcarbamoyl]-2-methyl-propylcarbamoyl}-4-tert-butoxycarbonylamino-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:

: 864238-48-2
(4S,5S)-isobutyl-5-methoxycarbonylethynyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

: 864238-64-2
4-{1-[1-(1-{[2-(1-benzyloxycarbonyl-ethylcarbamoyl)-cyclopentyl]-hydroxy-methyl}-3-methyl-butylcarbamoyl)-2-(trityl-carbamoyl)-ethylcarbamoyl]-2-methyl-propylcarbamoyl}-4-tert-butoxycarbonylamino-butyric acid benzyl ester

Guidance literature:: Multi-step reaction with 13 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: 210 mg / PyBOP; i-Pr₂NEt / CH₂Cl₂ / 4 h / 0 °C

8.1: TFA / CH₂Cl₂ / 1 h / 20 °C

9.1: 120 mg / PyBOP; i-Pr₂NEt / CH₂Cl₂ / 20 °C

10.1: HCl / dioxane / 2 h / 0 °C

11.1: 91 mg / PyBOP; i-Pr₂NEt / CH₂Cl₂ / 24 h / 20 °C

12.1: HCl / dioxane / 1 h / 0 °C

13.1: 63 mg / PyBOP; i-Pr₂NEt / N,N-dimethyl-acetamide / 24 h / 20 °C

With quinoline; hydrogenchloride; 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; 1,4-dioxane; methanol; dichloromethane; chloroform; N,N-dimethyl acetamide; toluene; benzene; 1.1: Lindlar reduction;
DOI:10.1021/jm050142+

Reference yield:

: (S)-2-[((1R,2R)-2-{(1S,2S)-2-[(S)-2-((S)-2-Amino-3-methyl-butyrylamino)-3-(trityl-carbamoyl)-propionylamino]-1-hydroxy-4-methyl-pentyl}-cyclopentanecarbonyl)-amino]-propionic acid benzyl ester

: 13574-13-5
Boc-Glu(OBzl)-OH

: 864238-64-2
4-{1-[1-(1-{[2-(1-benzyloxycarbonyl-ethylcarbamoyl)-cyclopentyl]-hydroxy-methyl}-3-methyl-butylcarbamoyl)-2-(trityl-carbamoyl)-ethylcarbamoyl]-2-methyl-propylcarbamoyl}-4-tert-butoxycarbonylamino-butyric acid benzyl ester

Guidance literature:: With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl acetamide; at 20 ℃; for 24h;
DOI:10.1021/jm050142+

Reference yield:

: 864238-49-3
(4S)-isobutyl-(5S)-(2-methoxycarbonyl-vinyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

: 864238-64-2
4-{1-[1-(1-{[2-(1-benzyloxycarbonyl-ethylcarbamoyl)-cyclopentyl]-hydroxy-methyl}-3-methyl-butylcarbamoyl)-2-(trityl-carbamoyl)-ethylcarbamoyl]-2-methyl-propylcarbamoyl}-4-tert-butoxycarbonylamino-butyric acid benzyl ester

Guidance literature:: Multi-step reaction with 12 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: 210 mg / PyBOP; i-Pr₂NEt / CH₂Cl₂ / 4 h / 0 °C

7.1: TFA / CH₂Cl₂ / 1 h / 20 °C

8.1: 120 mg / PyBOP; i-Pr₂NEt / CH₂Cl₂ / 20 °C

9.1: HCl / dioxane / 2 h / 0 °C

10.1: 91 mg / PyBOP; i-Pr₂NEt / CH₂Cl₂ / 24 h / 20 °C

11.1: HCl / dioxane / 1 h / 0 °C

12.1: 63 mg / PyBOP; i-Pr₂NEt / N,N-dimethyl-acetamide / 24 h / 20 °C

With hydrogenchloride; 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; 1,4-dioxane; methanol; dichloromethane; chloroform; N,N-dimethyl acetamide; toluene;
DOI:10.1021/jm050142+