cyclo[2,2-dimethyl-β-alanyl-(2S)-2-hydroxy-4-methylpentanoyl-(2E,5S,6R,7E)-5-hydroxy-8-[4-(methoxycarbonyl)phenyl]-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)-5-hydroxy-8-[4-(methoxycarbonyl)phenyl]-6-methyl-2,7-octadienoyl-3-chloro-O-methyl-D-tyrosyl]
• CAS No.: 204398-11-8
• Molecular Formula: C₃₈H₄₇ClN₂O₉
• Molecular Weight: 711.252
• Mol file: 204398-11-8.mol

Synonyms:cyclo[2,2-dimethyl-β-alanyl-(2S)-2-hydroxy-4-methylpentanoyl-(2E,5S,6R,7E)-5-hydroxy-8-[4-(methoxycarbonyl)phenyl]-6-methyl-2,7-octadienoyl-3-chloro-O-methyl-D-tyrosyl]

Chemical Property of cyclo[2,2-dimethyl-β-alanyl-(2S)-2-hydroxy-4-methylpentanoyl-(2E,5S,6R,7E)-5-hydroxy-8-[4-(methoxycarbonyl)phenyl]-6-methyl-2,7-octadienoyl-3-chloro-O-methyl-D-tyrosyl]

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of cyclo[2,2-dimethyl-β-alanyl-(2S)-2-hydroxy-4-methylpentanoyl-(2E,5S,6R,7E)-5-hydroxy-8-[4-(methoxycarbonyl)phenyl]-6-methyl-2,7-octadienoyl-3-chloro-O-methyl-D-tyrosyl]

There total 3 articles about cyclo[2,2-dimethyl-β-alanyl-(2S)-2-hydroxy-4-methylpentanoyl-(2E,5S,6R,7E)-5-hydroxy-8-[4-(methoxycarbonyl)phenyl]-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:

cryptophycin-51 (186256-66-6) → cyclo[2,2-dimethyl-β-alanyl-(2S)-2-hydroxy-4-methylpentanoyl-(2E,5S,6R,7E)-5-hydroxy-8-[4-(methoxycarbonyl)phenyl]-6-methyl-2,7-octadienoyl-3-chloro-O-methyl-D-tyrosyl] (204398-11-8)

Guidance literature:

Multi-step reaction with 4 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: sodium hydride / tetrahydrofuran / 1 h / 65 °C

4.2: 23 percent / tetrahydrofuran / 2 h / -78 - 20 °C

With sodium periodate; perchloric acid; sodium hydride; 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) → cyclo[2,2-dimethyl-β-alanyl-(2S)-2-hydroxy-4-methylpentanoyl-(2E,5S,6R,7E)-5-hydroxy-8-[4-(methoxycarbonyl)phenyl]-6-methyl-2,7-octadienoyl-3-chloro-O-methyl-D-tyrosyl] (204398-11-8)

Guidance literature:

Multi-step reaction with 3 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: sodium hydride / tetrahydrofuran / 1 h / 65 °C

3.2: 23 percent / tetrahydrofuran / 2 h / -78 - 20 °C

With sodium periodate; perchloric acid; sodium hydride; In tetrahydrofuran; 1,2-dimethoxyethane; 3.2: Wittig reaction;

DOI:10.1021/jm0203884

Reference yield:

(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 (214463-38-4) → cyclo[2,2-dimethyl-β-alanyl-(2S)-2-hydroxy-4-methylpentanoyl-(2E,5S,6R,7E)-5-hydroxy-8-[4-(methoxycarbonyl)phenyl]-6-methyl-2,7-octadienoyl-3-chloro-O-methyl-D-tyrosyl] (204398-11-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 98 percent / aq. NaIO₄ / tetrahydrofuran / 20 °C

2.1: sodium hydride / tetrahydrofuran / 1 h / 65 °C

2.2: 23 percent / tetrahydrofuran / 2 h / -78 - 20 °C

With sodium periodate; sodium hydride; In tetrahydrofuran; 2.2: Wittig reaction;

DOI:10.1021/jm0203884

upstream raw materials:

cryptophycin-51

cryptophycin 53

(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

Downstream raw materials:

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)-benzoic acid methyl ester