cyclo[2,2-dimethyl-β-alanyl-(2S)-2-hydroxy-4-methylpentanoyl-(2E,5S,6R,7E)-5-hydroxy-6-methyl-8-(3-methylphenyl)-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-6-methyl-8-(3-methylphenyl)-2,7-octadienoyl-3-chloro-O-methyl-D-tyrosyl]
• CAS No.: 204397-85-3
• Molecular Formula: C₃₇H₄₇ClN₂O₇
• Molecular Weight: 667.242
• Mol file: 204397-85-3.mol

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

There total 5 articles about cyclo[2,2-dimethyl-β-alanyl-(2S)-2-hydroxy-4-methylpentanoyl-(2E,5S,6R,7E)-5-hydroxy-6-methyl-8-(3-methylphenyl)-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: 58.0%

(3-methylbenzyl)triphenylphosphonium chloride (63368-37-6) + 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] (204397-62-6) → cyclo[2,2-dimethyl-β-alanyl-(2S)-2-hydroxy-4-methylpentanoyl-(2E,5S,6R,7E)-5-hydroxy-6-methyl-8-(3-methylphenyl)-2,7-octadienoyl-3-chloro-O-methyl-D-tyrosyl] (204397-85-3)

Guidance literature:

(3-methylbenzyl)triphenylphosphonium chloride; With n-butyllithium; In tetrahydrofuran; at -50 - 20 ℃;

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]; In tetrahydrofuran; at -78 - 20 ℃;

With thiophenol; 1,1'-azobis(1-cyanocyclohexanenitrile); In benzene; Heating;

DOI:10.1021/jm0203884

Reference yield: 58.0%

→ cyclo[2,2-dimethyl-β-alanyl-(2S)-2-hydroxy-4-methylpentanoyl-(2E,5S,6R,7E)-5-hydroxy-6-methyl-8-(3-methylphenyl)-2,7-octadienoyl-3-chloro-O-methyl-D-tyrosyl] (204397-85-3)

Guidance literature:

In styrene;

Reference yield:

cryptophycin-51 (186256-66-6) → cyclo[2,2-dimethyl-β-alanyl-(2S)-2-hydroxy-4-methylpentanoyl-(2E,5S,6R,7E)-5-hydroxy-6-methyl-8-(3-methylphenyl)-2,7-octadienoyl-3-chloro-O-methyl-D-tyrosyl] (204397-85-3)

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: n-butyllithium / tetrahydrofuran / -50 - 20 °C

4.2: tetrahydrofuran / -78 - 20 °C

4.3: 58 percent / 1,1'-azobis(cyclohexanecarbonitrile); thiophenol / benzene / Heating

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

DOI:10.1021/jm0203884

upstream raw materials:

(3-methylbenzyl)triphenylphosphonium chloride

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]

cryptophycin-51

cryptophycin 53

Downstream raw materials:

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