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)-

Base Information

• Chemical Name: 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)-
• CAS No.: 204398-06-1
• Molecular Formula: C₄₅H₆₂Cl₂N₄O₁₁
• Molecular Weight: 905.913

Synonyms: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)-

Chemical Property of 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)-

Chemical Property:

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Technology Process of 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)-

There total 11 articles about 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)- 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: 48.0%

C45H61ClN4O11 (204398-08-3) + C45H61ClN4O11 → 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)- (204398-06-1)

Guidance literature:

With chloro-trimethyl-silane; In chloroform; at -60 - 20 ℃; for 2h;

Reference yield:

{[4-(3-{(S)-1-[(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]-ethyl}-oxiranyl)-benzylcarbamoyl]-methyl}-methyl-carbamic acid tert-butyl 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)- (204398-06-1)

Guidance literature:

With chloro-trimethyl-silane; In chloroform; at -60 - 20 ℃;

DOI:10.1021/jm0203884

Reference yield:

cryptophycin-51 (186256-66-6) → 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)- (204398-06-1)

Guidance literature:

Multi-step reaction with 10 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

7.1: 57 percent / n-butylamine / ethanol / 48 h / 75 °C

8.1: 1-hydroxybenzotriazole hydrate; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / dimethylformamide / 0.75 h / 20 °C

8.2: 71 percent / dimethylformamide / 3 h / 20 °C

9.1: 3-chloroperoxybenzoic acid / CH₂Cl₂ / 20 °C

10.1: 0.1 g / chlorotrimethylsilane / CHCl₃ / -60 - 20 °C

With sodium periodate; n-butyllithium; chloro-trimethyl-silane; perchloric acid; tetrabutyl ammonium fluoride; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-butylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; 1,2-dimethoxyethane; ethanol; dichloromethane; chloroform; N,N-dimethyl-formamide; 4.2: Wittig reaction;

DOI:10.1021/jm0203884

upstream raw materials:

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]

(E)-(3S,10R,16S)-10-(3-Chloro-4-methoxy-benzyl)-16-((R)-2,3-dihydroxy-1-methyl-3-phenyl-propyl)-3-isobutyl-6,6-dimethyl-1,4-dioxa-8,11-diaza-cyclohexadec-13-ene-2,5,9,12-tetraone

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