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]

Base Information

Chemical Name: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]
CAS No.:204398-00-5
Molecular Formula:C₄₅H₅₀ClN₃O₉
Molecular Weight:812.36
Hs Code.:

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]

Synonyms: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]

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Chemical Property of 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]

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Technology Process of 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]

There total 6 articles about 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] 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: 90.0%

: 136918-14-4,85-41-6
phthalimide

: 204397-82-0
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)-

: 204398-00-5
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]

Guidance literature:: With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 20 ℃; for 2h;
DOI:10.1021/jm0203884

Reference yield:

: 186256-66-6
cryptophycin-51

: 204398-00-5
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]

Guidance literature:: Multi-step reaction with 6 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

6.1: 90 percent / triphenylphosphine; diethyl azodicarboxylate / tetrahydrofuran / 2 h / 20 °C

With sodium periodate; n-butyllithium; perchloric acid; tetrabutyl ammonium fluoride; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; 4.2: Wittig reaction;
DOI:10.1021/jm0203884

Reference yield:

: 186256-68-8
cryptophycin 53

: 204398-00-5
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]

Guidance literature:: Multi-step reaction with 5 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

5.1: 90 percent / triphenylphosphine; diethyl azodicarboxylate / tetrahydrofuran / 2 h / 20 °C

With sodium periodate; n-butyllithium; perchloric acid; tetrabutyl ammonium fluoride; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; 1,2-dimethoxyethane; 3.2: Wittig reaction;
DOI:10.1021/jm0203884