pentanoic acid, 3-chloro-N-[(2E,6S,7R,8S)-8-chloro-8-[4-[[4-[(1,1-dimethylethoxy)carbonyl]-1-piperazinyl]methyl]phenyl]-5,7-dihydroxy-6-methyl-1-oxo-2-octenyl]-O-methyl-D-tyrosyl-2,2-dimethyl-β-alanyl-2-hydroxy-4-methyl-, (3->1⁵)-lactone, (2S)-

Base Information

• Chemical Name: pentanoic acid, 3-chloro-N-[(2E,6S,7R,8S)-8-chloro-8-[4-[[4-[(1,1-dimethylethoxy)carbonyl]-1-piperazinyl]methyl]phenyl]-5,7-dihydroxy-6-methyl-1-oxo-2-octenyl]-O-methyl-D-tyrosyl-2,2-dimethyl-β-alanyl-2-hydroxy-4-methyl-, (3->1⁵)-lactone, (2S)-
• CAS No.: 204398-47-0
• Molecular Formula: C₄₆H₆₄Cl₂N₄O₁₀
• Molecular Weight: 903.941

Synonyms:pentanoic acid, 3-chloro-N-[(2E,6S,7R,8S)-8-chloro-8-[4-[[4-[(1,1-dimethylethoxy)carbonyl]-1-piperazinyl]methyl]phenyl]-5,7-dihydroxy-6-methyl-1-oxo-2-octenyl]-O-methyl-D-tyrosyl-2,2-dimethyl-β-alanyl-2-hydroxy-4-methyl-, (3->1⁵)-lactone, (2S)-

Chemical Property of pentanoic acid, 3-chloro-N-[(2E,6S,7R,8S)-8-chloro-8-[4-[[4-[(1,1-dimethylethoxy)carbonyl]-1-piperazinyl]methyl]phenyl]-5,7-dihydroxy-6-methyl-1-oxo-2-octenyl]-O-methyl-D-tyrosyl-2,2-dimethyl-β-alanyl-2-hydroxy-4-methyl-, (3->1⁵)-lactone, (2S)-

Chemical Property:

Purity/Quality:

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Technology Process of pentanoic acid, 3-chloro-N-[(2E,6S,7R,8S)-8-chloro-8-[4-[[4-[(1,1-dimethylethoxy)carbonyl]-1-piperazinyl]methyl]phenyl]-5,7-dihydroxy-6-methyl-1-oxo-2-octenyl]-O-methyl-D-tyrosyl-2,2-dimethyl-β-alanyl-2-hydroxy-4-methyl-, (3->1⁵)-lactone, (2S)-

There total 9 articles about pentanoic acid, 3-chloro-N-[(2E,6S,7R,8S)-8-chloro-8-[4-[[4-[(1,1-dimethylethoxy)carbonyl]-1-piperazinyl]methyl]phenyl]-5,7-dihydroxy-6-methyl-1-oxo-2-octenyl]-O-methyl-D-tyrosyl-2,2-dimethyl-β-alanyl-2-hydroxy-4-methyl-, (3->1⁵)-lactone, (2S)- 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: 92.0%

cyclo[2,2-dimethyl-β-alanyl-(2S)-2-hydroxy-4-methylpentanoyl-(2E,5S,6S)-6-[(2R,3R)-3-[4-[[4-[(1,1-dimethylethoxy)carbonyl]-1-piperazinyl]methyl]phenyl]oxiranyl]-5-hydroxy-2-heptenoyl-3-chloro-O-methyl-D-tyrosyl] (204398-46-9) → pentanoic acid, 3-chloro-N-[(2E,6S,7R,8S)-8-chloro-8-[4-[[4-[(1,1-dimethylethoxy)carbonyl]-1-piperazinyl]methyl]phenyl]-5,7-dihydroxy-6-methyl-1-oxo-2-octenyl]-O-methyl-D-tyrosyl-2,2-dimethyl-β-alanyl-2-hydroxy-4-methyl-, (3->15)-lactone, (2S)- (204398-47-0)

Guidance literature:

With chloro-trimethyl-silane; In chloroform; at -66 - 20 ℃;

DOI:10.1021/jm0203884

Reference yield:

cryptophycin-51 (186256-66-6) → pentanoic acid, 3-chloro-N-[(2E,6S,7R,8S)-8-chloro-8-[4-[[4-[(1,1-dimethylethoxy)carbonyl]-1-piperazinyl]methyl]phenyl]-5,7-dihydroxy-6-methyl-1-oxo-2-octenyl]-O-methyl-D-tyrosyl-2,2-dimethyl-β-alanyl-2-hydroxy-4-methyl-, (3->15)-lactone, (2S)- (204398-47-0)

Guidance literature:

Multi-step reaction with 9 steps

1.1: m-chloroperbenzoic acid / CH₂Cl₂ / 20 °C

2.1: 72 percent / aq. perchloric acid / 1,2-dimethoxy-ethane / 6 h / 20 °C

3.1: 98 percent / aq. NaIO₄ / tetrahydrofuran / 20 °C

4.1: n-butyllithium / tetrahydrofuran / 0.5 h / -50 - 20 °C

4.2: tetrahydrofuran / 3.75 h / -78 - 20 °C

4.3: 6.7 g / 1,1'-azobis(cyclohexanecarbonitrile); thiophenol / benzene / 5 h / Heating

5.1: 0.67 g / 3-chloroperoxybenzoic acid / CH₂Cl₂ / 0 - 20 °C

6.1: 84 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0 - 20 °C

7.1: 0.26 g / N-chlorosuccinimide; triphenylphosphine; NaHCO₃ / CH₂Cl₂ / 0.33 h / 0 °C

8.1: 81 percent / tetrahydrofuran / 20 °C

9.1: 92 percent / chlorotrimethylsilane / CHCl₃ / -66 - 20 °C

With sodium periodate; N-chloro-succinimide; n-butyllithium; chloro-trimethyl-silane; perchloric acid; tetrabutyl ammonium fluoride; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; chloroform; 4.2: Wittig reaction;

DOI:10.1021/jm0203884

Reference yield:

cryptophycin 53 (186256-68-8) → pentanoic acid, 3-chloro-N-[(2E,6S,7R,8S)-8-chloro-8-[4-[[4-[(1,1-dimethylethoxy)carbonyl]-1-piperazinyl]methyl]phenyl]-5,7-dihydroxy-6-methyl-1-oxo-2-octenyl]-O-methyl-D-tyrosyl-2,2-dimethyl-β-alanyl-2-hydroxy-4-methyl-, (3->15)-lactone, (2S)- (204398-47-0)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 72 percent / aq. perchloric acid / 1,2-dimethoxy-ethane / 6 h / 20 °C

2.1: 98 percent / aq. NaIO₄ / tetrahydrofuran / 20 °C

3.1: n-butyllithium / tetrahydrofuran / 0.5 h / -50 - 20 °C

3.2: tetrahydrofuran / 3.75 h / -78 - 20 °C

3.3: 6.7 g / 1,1'-azobis(cyclohexanecarbonitrile); thiophenol / benzene / 5 h / Heating

4.1: 0.67 g / 3-chloroperoxybenzoic acid / CH₂Cl₂ / 0 - 20 °C

5.1: 84 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0 - 20 °C

6.1: 0.26 g / N-chlorosuccinimide; triphenylphosphine; NaHCO₃ / CH₂Cl₂ / 0.33 h / 0 °C

7.1: 81 percent / tetrahydrofuran / 20 °C

8.1: 92 percent / chlorotrimethylsilane / CHCl₃ / -66 - 20 °C

With sodium periodate; N-chloro-succinimide; n-butyllithium; chloro-trimethyl-silane; perchloric acid; tetrabutyl ammonium fluoride; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; chloroform; 3.2: Wittig reaction;

DOI:10.1021/jm0203884

upstream raw materials:

cyclo[2,2-dimethyl-β-alanyl-(2S)-2-hydroxy-4-methylpentanoyl-(2E,5S,6S)-6-[(2R,3R)-3-[4-[[4-[(1,1-dimethylethoxy)carbonyl]-1-piperazinyl]methyl]phenyl]oxiranyl]-5-hydroxy-2-heptenoyl-3-chloro-O-methyl-D-tyrosyl]

cryptophycin-51

cryptophycin 53

cyclo[2,2-dimethyl-β-alanyl-(2S)-2-hydroxy-4-methylpentanoyl-(2E,5S,6S)-5-hydroxy-6-methyl-7-oxo-2-heptenoyl-3-chloro-O-methyl-D-tyrosyl]

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