pentanoic acid, 3-chloro-N-[(2E,5S,6R,7E)-5-hydroxy-8-[4-(hydroxymethyl)phenyl]-6-methyl-1-oxo-2,7-octadienyl]-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,5S,6R,7E)-5-hydroxy-8-[4-(hydroxymethyl)phenyl]-6-methyl-1-oxo-2,7-octadienyl]-O-methyl-D-tyrosyl-2,2-dimethyl-β-alanyl-2-hydroxy-4-methyl-, (3->1⁵)-lactone, (2S)-
• CAS No.: 204397-82-0
• Molecular Formula: C₃₇H₄₇ClN₂O₈
• Molecular Weight: 683.242

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

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

There total 5 articles about pentanoic acid, 3-chloro-N-[(2E,5S,6R,7E)-5-hydroxy-8-[4-(hydroxymethyl)phenyl]-6-methyl-1-oxo-2,7-octadienyl]-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: 99.0%

cyclo[2,2-dimethyl-β-alanyl-(2S)-2-hydroxy-4-methylpentanoyl-(2E,5S,6R,7E)-5-hydroxy-6-methyl-8-[4-[[[tris(1-methylethyl)silyl]oxy]methyl]phenyl]-2,7-octadienoyl-3-chloro-O-methyl-D-tyrosyl] (204397-65-9) → pentanoic acid, 3-chloro-N-[(2E,5S,6R,7E)-5-hydroxy-8-[4-(hydroxymethyl)phenyl]-6-methyl-1-oxo-2,7-octadienyl]-O-methyl-D-tyrosyl-2,2-dimethyl-β-alanyl-2-hydroxy-4-methyl-, (3->15)-lactone, (2S)- (204397-82-0)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at -78 - 20 ℃; for 0.666667h;

DOI:10.1021/jm0203884

Reference yield:

cryptophycin-51 (186256-66-6) → pentanoic acid, 3-chloro-N-[(2E,5S,6R,7E)-5-hydroxy-8-[4-(hydroxymethyl)phenyl]-6-methyl-1-oxo-2,7-octadienyl]-O-methyl-D-tyrosyl-2,2-dimethyl-β-alanyl-2-hydroxy-4-methyl-, (3->15)-lactone, (2S)- (204397-82-0)

Guidance literature:

Multi-step reaction with 5 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: 99 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.67 h / -78 - 20 °C

With sodium periodate; n-butyllithium; perchloric acid; tetrabutyl ammonium fluoride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; 4.2: Wittig reaction;

DOI:10.1021/jm0203884

Reference yield:

cryptophycin 53 (186256-68-8) → pentanoic acid, 3-chloro-N-[(2E,5S,6R,7E)-5-hydroxy-8-[4-(hydroxymethyl)phenyl]-6-methyl-1-oxo-2,7-octadienyl]-O-methyl-D-tyrosyl-2,2-dimethyl-β-alanyl-2-hydroxy-4-methyl-, (3->15)-lactone, (2S)- (204397-82-0)

Guidance literature:

Multi-step reaction with 4 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: 99 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.67 h / -78 - 20 °C

With sodium periodate; n-butyllithium; perchloric acid; tetrabutyl ammonium fluoride; In tetrahydrofuran; 1,2-dimethoxyethane; 3.2: Wittig reaction;

DOI:10.1021/jm0203884

upstream raw materials:

cyclo[2,2-dimethyl-β-alanyl-(2S)-2-hydroxy-4-methylpentanoyl-(2E,5S,6R,7E)-5-hydroxy-6-methyl-8-[4-[[[tris(1-methylethyl)silyl]oxy]methyl]phenyl]-2,7-octadienoyl-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]

Downstream raw materials:

cyclo[2,2-dimethyl-β-alanyl-(2S)-2-hydroxy-4-methylpentanoyl-(2E,5S,6R,7E)-8-[4-[(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)methyl]phenyl]-5-hydroxy-6-methyl-2,7-octadienoyl-3-chloro-O-methyl-D-tyrosyl]

cyclo[2,2-dimethyl-β-alanyl-(2S)-2-hydroxy-4-methylpentanoyl-(2E,5S,6R,7E)-8-[4-[[3-[[(1,1-dimethylethoxy)carbonyl]amino]-2,2-dimethyl-1-oxopropoxy]methyl]phenyl]-5-hydroxy-6-methyl-2,7-octadienoyl-3-chloro-O-methyl-D-tyrosyl]

3-tert-Butoxycarbonylamino-2,2-dimethyl-propionic acid 4-{(1S,2R,3R)-1-chloro-3-[(E)-(3S,10R,16S)-10-(3-chloro-4-methoxy-benzyl)-3-isobutyl-6,6-dimethyl-2,5,9,12-tetraoxo-1,4-dioxa-8,11-diaza-cyclohexadec-13-en-16-yl]-2-hydroxy-butyl}-benzyl ester

pentanoic acid, N-[(1,1-dimethylethoxy)carbonyl]-N-methylglycyl-(2E,5S,6S,7R,8S)-8-[4-(aminomethyl)phenyl]-8-chloro-5,7-dihydroxy-6-methyl-2-octenoyl-3-chloro-O-methyl-D-tyrosyl-2,2-dimethyl-β-alanyl-2-hydroxy-4-methyl-, (5->2⁵)-lactone, (2S)-

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