cyclo[2,2-dimethyl-β-alanyl-(2S)-2-hydroxy-4-methylpentanoyl-(2E,5S,6R,7E)-5-hydroxy-6-methyl-8-(2-methyl-5-thiazolyl)-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-(2-methyl-5-thiazolyl)-2,7-octadienoyl-3-chloro-O-methyl-D-tyrosyl]
CAS No.:204398-55-0
Molecular Formula:C₃₄H₄₄ClN₃O₇S
Molecular Weight:674.258
Hs Code.:

cyclo[2,2-dimethyl-β-alanyl-(2S)-2-hydroxy-4-methylpentanoyl-(2E,5S,6R,7E)-5-hydroxy-6-methyl-8-(2-methyl-5-thiazolyl)-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)-5-hydroxy-6-methyl-8-(2-methyl-5-thiazolyl)-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)-5-hydroxy-6-methyl-8-(2-methyl-5-thiazolyl)-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)-5-hydroxy-6-methyl-8-(2-methyl-5-thiazolyl)-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-(2-methyl-5-thiazolyl)-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: 34.0%

: cryptophycin 55 (L)-alaninate hydrochloride

: [(2-methyl-4-thiazolyl)methyl]triphenylphosphonium chloride

: 204398-55-0
cyclo[2,2-dimethyl-β-alanyl-(2S)-2-hydroxy-4-methylpentanoyl-(2E,5S,6R,7E)-5-hydroxy-6-methyl-8-(2-methyl-5-thiazolyl)-2,7-octadienoyl-3-chloro-O-methyl-D-tyrosyl]

Guidance literature:: [(2-methyl-4-thiazolyl)methyl]triphenylphosphonium chloride; With n-butyllithium; In tetrahydrofuran; at -78 - 20 ℃; for 0.75h;

cryptophycin 55 (L)-alaninate hydrochloride; In tetrahydrofuran; at -78 - 20 ℃; for 3.5h;

Reference yield: 34.0%

: [(2-methyl-4-thiazolyl)methyl]triphenylphosphonium chloride

: 204397-62-6
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]

: 204398-55-0
cyclo[2,2-dimethyl-β-alanyl-(2S)-2-hydroxy-4-methylpentanoyl-(2E,5S,6R,7E)-5-hydroxy-6-methyl-8-(2-methyl-5-thiazolyl)-2,7-octadienoyl-3-chloro-O-methyl-D-tyrosyl]

Guidance literature:: [(2-methyl-4-thiazolyl)methyl]triphenylphosphonium chloride; With n-butyllithium; In tetrahydrofuran; at -78 - 20 ℃; for 0.75h;

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 ℃; for 3.5h;
DOI:10.1021/jm0203884

Reference yield:

: 186256-66-6
cryptophycin-51

: 204398-55-0
cyclo[2,2-dimethyl-β-alanyl-(2S)-2-hydroxy-4-methylpentanoyl-(2E,5S,6R,7E)-5-hydroxy-6-methyl-8-(2-methyl-5-thiazolyl)-2,7-octadienoyl-3-chloro-O-methyl-D-tyrosyl]

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 / 0.75 h / -78 - 20 °C

4.2: 34 percent / tetrahydrofuran / 3.5 h / -78 - 20 °C

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