(S)-2-((S)-2-{[(1R,2R)-2-((4S,5S)-3-tert-Butoxycarbonyl-4-isobutyl-2,2-dimethyl-oxazolidin-5-yl)-cyclopentanecarbonyl]-amino}-propionylamino)-pentanedioic acid dibenzyl ester

Base Information

• Chemical Name: (S)-2-((S)-2-{[(1R,2R)-2-((4S,5S)-3-tert-Butoxycarbonyl-4-isobutyl-2,2-dimethyl-oxazolidin-5-yl)-cyclopentanecarbonyl]-amino}-propionylamino)-pentanedioic acid dibenzyl ester
• CAS No.: 864238-54-0
• Molecular Formula: C₄₂H₅₉N₃O₉
• Molecular Weight: 749.945

Synonyms:(S)-2-((S)-2-{[(1R,2R)-2-((4S,5S)-3-tert-Butoxycarbonyl-4-isobutyl-2,2-dimethyl-oxazolidin-5-yl)-cyclopentanecarbonyl]-amino}-propionylamino)-pentanedioic acid dibenzyl ester

Chemical Property of (S)-2-((S)-2-{[(1R,2R)-2-((4S,5S)-3-tert-Butoxycarbonyl-4-isobutyl-2,2-dimethyl-oxazolidin-5-yl)-cyclopentanecarbonyl]-amino}-propionylamino)-pentanedioic acid dibenzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-((S)-2-{[(1R,2R)-2-((4S,5S)-3-tert-Butoxycarbonyl-4-isobutyl-2,2-dimethyl-oxazolidin-5-yl)-cyclopentanecarbonyl]-amino}-propionylamino)-pentanedioic acid dibenzyl ester

There total 9 articles about (S)-2-((S)-2-{[(1R,2R)-2-((4S,5S)-3-tert-Butoxycarbonyl-4-isobutyl-2,2-dimethyl-oxazolidin-5-yl)-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-((4S,5S)-3-tert-Butoxycarbonyl-4-isobutyl-2,2-dimethyl-oxazolidin-5-yl)-cyclopentanecarbonyl]-amino}-propionylamino)-pentanedioic acid dibenzyl ester (864238-54-0)

Guidance literature:

Multi-step reaction with 7 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

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; 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:

tert-butoxycarbonyl-L-leucinal (58521-45-2) → (S)-2-((S)-2-{[(1R,2R)-2-((4S,5S)-3-tert-Butoxycarbonyl-4-isobutyl-2,2-dimethyl-oxazolidin-5-yl)-cyclopentanecarbonyl]-amino}-propionylamino)-pentanedioic acid dibenzyl ester (864238-54-0)

Guidance literature:

Multi-step reaction with 9 steps

1.1: LDA / hexane; tetrahydrofuran / 0.5 h / -78 °C

1.2: 72 percent / CeCl₃ / hexane; tetrahydrofuran / 3 h / -78 °C

2.1: acetone / 0.08 h / Heating

2.2: 64 percent / TsOH / acetone / 2 h / Heating

3.1: 90 percent / quinoline; H₂ / Lindlar catalyst / benzene / 20 °C

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

4.2: 0.85 g / NaOMe / methanol / 6 h / Heating

5.1: 90 percent / aq. NaIO₄; OsO₄ / tetrahydrofuran / 14 h / 20 °C

6.1: 99 percent / Na₂SO₄ / methanol / 2 h / Heating

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

7.2: 68 percent / NaOAc*3H₂O / CHCl₃; tetrahydrofuran / 3 h / Heating

8.1: aq. KOH / methanol / 3 h / 65 °C

9.1: 124 mg / PyBOP; i-Pr₂NEt / CH₂Cl₂ / 4 h / 0 °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; lithium diisopropyl amide; benzo[1,3,2]dioxaborole; Lindlar's catalyst; In tetrahydrofuran; methanol; hexane; dichloromethane; chloroform; acetone; toluene; benzene; 3.1: Lindlar reduction;

DOI:10.1021/jm050142+

Reference yield:

(5S)-tert-butoxycarbonylamino-(4S,R)-hydroxy-7-methyl-oct-2-ynoic acid methyl ester (728947-30-6) → (S)-2-((S)-2-{[(1R,2R)-2-((4S,5S)-3-tert-Butoxycarbonyl-4-isobutyl-2,2-dimethyl-oxazolidin-5-yl)-cyclopentanecarbonyl]-amino}-propionylamino)-pentanedioic acid dibenzyl ester (864238-54-0)

Guidance literature:

Multi-step reaction with 8 steps

1.1: acetone / 0.08 h / Heating

1.2: 64 percent / TsOH / acetone / 2 h / Heating

2.1: 90 percent / quinoline; H₂ / Lindlar catalyst / benzene / 20 °C

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

3.2: 0.85 g / NaOMe / methanol / 6 h / Heating

4.1: 90 percent / aq. NaIO₄; OsO₄ / tetrahydrofuran / 14 h / 20 °C

5.1: 99 percent / Na₂SO₄ / methanol / 2 h / Heating

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

6.2: 68 percent / NaOAc*3H₂O / CHCl₃; tetrahydrofuran / 3 h / Heating

7.1: aq. KOH / methanol / 3 h / 65 °C

8.1: 124 mg / PyBOP; i-Pr₂NEt / CH₂Cl₂ / 4 h / 0 °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; benzo[1,3,2]dioxaborole; Lindlar's catalyst; In tetrahydrofuran; methanol; dichloromethane; chloroform; acetone; toluene; benzene; 2.1: Lindlar reduction;

DOI:10.1021/jm050142+

upstream raw materials:

(4S,5S)-5-((1R,2R)-2-Carboxy-cyclopentyl)-4-isobutyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

H-Ala-Glu(OBn)-OBn

(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

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

(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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