(S)-2-{(S)-2-[((1R,2R)-2-{(1S,2S)-2-[(S)-2-tert-Butoxycarbonylamino-3-(trityl-carbamoyl)-propionylamino]-1-hydroxy-4-methyl-pentyl}-cyclopentanecarbonyl)-amino]-propionylamino}-pentanedioic acid dibenzyl ester

Base Information

• Chemical Name: (S)-2-{(S)-2-[((1R,2R)-2-{(1S,2S)-2-[(S)-2-tert-Butoxycarbonylamino-3-(trityl-carbamoyl)-propionylamino]-1-hydroxy-4-methyl-pentyl}-cyclopentanecarbonyl)-amino]-propionylamino}-pentanedioic acid dibenzyl ester
• CAS No.: 864238-57-3
• Molecular Formula: C₆₂H₇₅N₅O₁₁
• Molecular Weight: 1066.3

Synonyms:(S)-2-{(S)-2-[((1R,2R)-2-{(1S,2S)-2-[(S)-2-tert-Butoxycarbonylamino-3-(trityl-carbamoyl)-propionylamino]-1-hydroxy-4-methyl-pentyl}-cyclopentanecarbonyl)-amino]-propionylamino}-pentanedioic acid dibenzyl ester

Chemical Property of (S)-2-{(S)-2-[((1R,2R)-2-{(1S,2S)-2-[(S)-2-tert-Butoxycarbonylamino-3-(trityl-carbamoyl)-propionylamino]-1-hydroxy-4-methyl-pentyl}-cyclopentanecarbonyl)-amino]-propionylamino}-pentanedioic acid dibenzyl ester

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Technology Process of (S)-2-{(S)-2-[((1R,2R)-2-{(1S,2S)-2-[(S)-2-tert-Butoxycarbonylamino-3-(trityl-carbamoyl)-propionylamino]-1-hydroxy-4-methyl-pentyl}-cyclopentanecarbonyl)-amino]-propionylamino}-pentanedioic acid dibenzyl ester

There total 9 articles about (S)-2-{(S)-2-[((1R,2R)-2-{(1S,2S)-2-[(S)-2-tert-Butoxycarbonylamino-3-(trityl-carbamoyl)-propionylamino]-1-hydroxy-4-methyl-pentyl}-cyclopentanecarbonyl)-amino]-propionylamino}-pentanedioic acid dibenzyl 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) → (S)-2-{(S)-2-[((1R,2R)-2-{(1S,2S)-2-[(S)-2-tert-Butoxycarbonylamino-3-(trityl-carbamoyl)-propionylamino]-1-hydroxy-4-methyl-pentyl}-cyclopentanecarbonyl)-amino]-propionylamino}-pentanedioic acid dibenzyl ester (864238-57-3)

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

8.1: TFA / CH₂Cl₂ / 1 h / 20 °C

9.1: 110 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)-2-((S)-2-{[(1R,2R)-2-((1S,2S)-2-Amino-1-hydroxy-4-methyl-pentyl)-cyclopentanecarbonyl]-amino}-propionylamino)-pentanedioic acid dibenzyl ester + Nα-tert-butoxycarbonyl-Nω-triphenylmethyl-L-asparagine (132388-68-2) → (S)-2-{(S)-2-[((1R,2R)-2-{(1S,2S)-2-[(S)-2-tert-Butoxycarbonylamino-3-(trityl-carbamoyl)-propionylamino]-1-hydroxy-4-methyl-pentyl}-cyclopentanecarbonyl)-amino]-propionylamino}-pentanedioic acid dibenzyl ester (864238-57-3)

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) → (S)-2-{(S)-2-[((1R,2R)-2-{(1S,2S)-2-[(S)-2-tert-Butoxycarbonylamino-3-(trityl-carbamoyl)-propionylamino]-1-hydroxy-4-methyl-pentyl}-cyclopentanecarbonyl)-amino]-propionylamino}-pentanedioic acid dibenzyl ester (864238-57-3)

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

7.1: TFA / CH₂Cl₂ / 1 h / 20 °C

8.1: 110 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:

(S)-2-{(S)-2-[((1R,2R)-2-{(1S,2S)-2-[(S)-2-((S)-2-tert-Butoxycarbonylamino-3-methyl-butyrylamino)-3-(trityl-carbamoyl)-propionylamino]-1-hydroxy-4-methyl-pentyl}-cyclopentanecarbonyl)-amino]-propionylamino}-pentanedioic acid dibenzyl ester

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