(16S,17S,18R)-17,18-Bis(trimethylsilylethoxymethoxy)-16,18-dimethyl-10-phenyl[11]cytochalasa-6⁽⁷⁾,13-diene-1,21-dione

Base Information

• Chemical Name: (16S,17S,18R)-17,18-Bis(trimethylsilylethoxymethoxy)-16,18-dimethyl-10-phenyl[11]cytochalasa-6⁽⁷⁾,13-diene-1,21-dione
• CAS No.: 129056-23-1
• Molecular Formula: C₄₀H₆₅NO₆Si₂
• Molecular Weight: 712.13

Synonyms:(16S,17S,18R)-17,18-Bis(trimethylsilylethoxymethoxy)-16,18-dimethyl-10-phenyl[11]cytochalasa-6⁽⁷⁾,13-diene-1,21-dione

Chemical Property of (16S,17S,18R)-17,18-Bis(trimethylsilylethoxymethoxy)-16,18-dimethyl-10-phenyl[11]cytochalasa-6⁽⁷⁾,13-diene-1,21-dione

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Technology Process of (16S,17S,18R)-17,18-Bis(trimethylsilylethoxymethoxy)-16,18-dimethyl-10-phenyl[11]cytochalasa-6⁽⁷⁾,13-diene-1,21-dione

There total 4 articles about (16S,17S,18R)-17,18-Bis(trimethylsilylethoxymethoxy)-16,18-dimethyl-10-phenyl[11]cytochalasa-6⁽⁷⁾,13-diene-1,21-dione 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: 89.0%

(16S,17S,18R)-2-Benzoyl-17,18-bis(trimethylsilylethoxymethoxy)-16,18-dimethyl-10-phenyl[11]cytochalasa-6(7),13-diene-1,21-dione (129056-22-0) → (16S,17S,18R)-17,18-Bis(trimethylsilylethoxymethoxy)-16,18-dimethyl-10-phenyl[11]cytochalasa-6(7),13-diene-1,21-dione (129056-23-1)

Guidance literature:

With sodium hydroxide; water; In methanol; for 2.5h;

DOI:10.1039/a906414a

Reference yield:

(R)-1-Benzoyl-5-benzyl-3-[(8E,10E,12E)-(4R,5S,6S)-4,6,12-trimethyl-4,5-bis-(2-trimethylsilanyl-ethoxymethoxy)-tetradeca-8,10,12-trienoyl]-pyrrolidin-2-one → (16S,17S,18R)-17,18-Bis(trimethylsilylethoxymethoxy)-16,18-dimethyl-10-phenyl[11]cytochalasa-6(7),13-diene-1,21-dione (129056-23-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: LiN(SiMe₃)2 / tetrahydrofuran / 0.5 h / -72 °C

1.2: 81 percent / tetrahydrofuran / 2.5 h / -72 °C

2.1: H₂O₂; MCPBA / CHCl₃; H₂O / 0.42 h / -50 - 0 °C

3.1: toluene / 16 h / 80 °C

4.1: 89 percent / NaOH; H₂O / methanol / 2.5 h

With sodium hydroxide; water; dihydrogen peroxide; 3-chloro-benzenecarboperoxoic acid; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; chloroform; water; toluene; 1.1: Metallation / 1.2: Phenylselenation / 2.1: Elimination / 3.1: Cycloaddition / 4.1: Hydrolysis;

DOI:10.1039/a906414a

Reference yield:

(S)-1-Benzoyl-5-benzyl-3-[(8E,10E,12E)-(4R,5S,6S)-4,6,12-trimethyl-4,5-bis-(2-trimethylsilanyl-ethoxymethoxy)-tetradeca-8,10,12-trienoyl]-1,5-dihydro-pyrrol-2-one (129056-21-9) → (16S,17S,18R)-17,18-Bis(trimethylsilylethoxymethoxy)-16,18-dimethyl-10-phenyl[11]cytochalasa-6(7),13-diene-1,21-dione (129056-23-1)

Guidance literature:

Multi-step reaction with 2 steps

1: toluene / 16 h / 80 °C

2: 89 percent / NaOH; H₂O / methanol / 2.5 h

With sodium hydroxide; water; In methanol; toluene; 1: Cycloaddition / 2: Hydrolysis;

DOI:10.1039/a906414a

upstream raw materials:

(16S,17S,18R)-2-Benzoyl-17,18-bis(trimethylsilylethoxymethoxy)-16,18-dimethyl-10-phenyl[11]cytochalasa-6⁽⁷⁾,13-diene-1,21-dione

(S)-1-Benzoyl-5-benzyl-3-[(8E,10E,12E)-(4R,5S,6S)-4,6,12-trimethyl-4,5-bis-(2-trimethylsilanyl-ethoxymethoxy)-tetradeca-8,10,12-trienoyl]-1,5-dihydro-pyrrol-2-one

(5S)-1-Benzoyl-3-[(4R,5S,6S,8E,10E,12E)-4,5-bis(trimethylsilylethoxymethoxy)-1-oxo-4,6,12-trimethyltetradeca-8,10,12-trienyl]-5-phenylmethyl-3-phenylselenopyrrolidin-2-one

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