5(S)-[(tert-butyldiphenylsilyl)oxy]-12(R)-[(triethylsilyl)oxy]-8(E),10(E)-eicosadien-6,14-diynoic acid methyl ester

Base Information

Chemical Name:5(S)-[(tert-butyldiphenylsilyl)oxy]-12(R)-[(triethylsilyl)oxy]-8(E),10(E)-eicosadien-6,14-diynoic acid methyl ester
CAS No.:329897-01-0
Molecular Formula:C₄₃H₆₂O₄Si₂
Molecular Weight:699.134
Hs Code.:

Synonyms:5(S)-[(tert-butyldiphenylsilyl)oxy]-12(R)-[(triethylsilyl)oxy]-8(E),10(E)-eicosadien-6,14-diynoic acid methyl ester

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Chemical Property of 5(S)-[(tert-butyldiphenylsilyl)oxy]-12(R)-[(triethylsilyl)oxy]-8(E),10(E)-eicosadien-6,14-diynoic acid methyl ester

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Technology Process of 5(S)-[(tert-butyldiphenylsilyl)oxy]-12(R)-[(triethylsilyl)oxy]-8(E),10(E)-eicosadien-6,14-diynoic acid methyl ester

There total 3 articles about 5(S)-[(tert-butyldiphenylsilyl)oxy]-12(R)-[(triethylsilyl)oxy]-8(E),10(E)-eicosadien-6,14-diynoic acid methyl ester 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: 49.0%

: 90108-25-1
(E)-(S)-5-(tert-Butyl-diphenyl-silanyloxy)-10-(dimethoxy-phosphoryl)-dec-8-en-6-ynoic acid methyl ester

: 245326-02-7
(R)-2-[(triethylsilyl)oxy]-4-decynal

: 329897-01-0
5(S)-[(tert-butyldiphenylsilyl)oxy]-12(R)-[(triethylsilyl)oxy]-8(E),10(E)-eicosadien-6,14-diynoic acid methyl ester

Guidance literature:: (E)-(S)-5-(tert-Butyl-diphenyl-silanyloxy)-10-(dimethoxy-phosphoryl)-dec-8-en-6-ynoic acid methyl ester; (R)-2-[(triethylsilyl)oxy]-4-decynal; With lithium diisopropyl amide; In tetrahydrofuran; cyclohexane; at -78 - 20 ℃; for 1h;

With iodine; In dichloromethane; at 20 ℃; for 0.5h;
DOI:10.1016/S0040-4020(00)00983-2

Reference yield:

: 329896-85-7
(R)-1-[(triethylsilyl)oxy]-4-decyn-2-ol

: 329897-01-0
5(S)-[(tert-butyldiphenylsilyl)oxy]-12(R)-[(triethylsilyl)oxy]-8(E),10(E)-eicosadien-6,14-diynoic acid methyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: 64 percent / imidazole; Et₃N / dimethylformamide / 0.5 h / 0 °C

2.1: 68 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 0.67 h / -70 - -40 °C

3.1: LDA / tetrahydrofuran; cyclohexane / 1 h / -78 - 20 °C

3.2: 49 percent / I₂ / CH₂Cl₂ / 0.5 h / 20 °C

With 1H-imidazole; oxalyl dichloride; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; cyclohexane; N,N-dimethyl-formamide; 2.1: Swern conditions;
DOI:10.1016/S0040-4020(00)00983-2

Reference yield:

: 245325-94-4
(R)-1,2-bis[(triethylsilyl)oxy]-4-decyne

: 329897-01-0
5(S)-[(tert-butyldiphenylsilyl)oxy]-12(R)-[(triethylsilyl)oxy]-8(E),10(E)-eicosadien-6,14-diynoic acid methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: 68 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 0.67 h / -70 - -40 °C

2.1: LDA / tetrahydrofuran; cyclohexane / 1 h / -78 - 20 °C

2.2: 49 percent / I₂ / CH₂Cl₂ / 0.5 h / 20 °C

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; cyclohexane; 1.1: Swern conditions;
DOI:10.1016/S0040-4020(00)00983-2