(S)-3-[(9Z,15E,19E)-(2R,12S)-2-(tert-Butyl-diphenyl-silanyloxy)-12-hydroxy-dotriaconta-9,15,19-trienyl]-5-methyl-5H-furan-2-one

Base Information

Chemical Name:(S)-3-[(9Z,15E,19E)-(2R,12S)-2-(tert-Butyl-diphenyl-silanyloxy)-12-hydroxy-dotriaconta-9,15,19-trienyl]-5-methyl-5H-furan-2-one
CAS No.:358740-37-1
Molecular Formula:C₅₃H₈₂O₄Si
Molecular Weight:811.317
Hs Code.:

Synonyms:(S)-3-[(9Z,15E,19E)-(2R,12S)-2-(tert-Butyl-diphenyl-silanyloxy)-12-hydroxy-dotriaconta-9,15,19-trienyl]-5-methyl-5H-furan-2-one

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Chemical Property of (S)-3-[(9Z,15E,19E)-(2R,12S)-2-(tert-Butyl-diphenyl-silanyloxy)-12-hydroxy-dotriaconta-9,15,19-trienyl]-5-methyl-5H-furan-2-one

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Technology Process of (S)-3-[(9Z,15E,19E)-(2R,12S)-2-(tert-Butyl-diphenyl-silanyloxy)-12-hydroxy-dotriaconta-9,15,19-trienyl]-5-methyl-5H-furan-2-one

There total 8 articles about (S)-3-[(9Z,15E,19E)-(2R,12S)-2-(tert-Butyl-diphenyl-silanyloxy)-12-hydroxy-dotriaconta-9,15,19-trienyl]-5-methyl-5H-furan-2-one 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: 61.0%

: 358740-35-9
(S)-3-[(9Z,15E,19E)-(2R,12S)-2-(tert-Butyl-diphenyl-silanyloxy)-12-methoxymethoxy-dotriaconta-9,15,19-trienyl]-5-methyl-5H-furan-2-one

: 358740-37-1
(S)-3-[(9Z,15E,19E)-(2R,12S)-2-(tert-Butyl-diphenyl-silanyloxy)-12-hydroxy-dotriaconta-9,15,19-trienyl]-5-methyl-5H-furan-2-one

Guidance literature:: With trimethylsilyl bromide; In dichloromethane; at -30 ℃; for 0.5h;
DOI:10.1016/S0040-4020(01)00381-7

Reference yield:

: 358740-29-1
(2S,3S,6E,10E)-2,3-epoxytricosa-6,10-dien-1-ol

: 358740-37-1
(S)-3-[(9Z,15E,19E)-(2R,12S)-2-(tert-Butyl-diphenyl-silanyloxy)-12-hydroxy-dotriaconta-9,15,19-trienyl]-5-methyl-5H-furan-2-one

Guidance literature:: Multi-step reaction with 8 steps

1: 97 percent / Red-Al / tetrahydrofuran / 4 h / 0 °C

2: i-Pr₂NEt; DMAP / CH₂Cl₂ / 18 h / 20 °C

3: 5.8 g / i-Pr₂NEt; DMAP / CH₂Cl₂ / 22 h / 20 °C

4: 94 percent / TBAF / tetrahydrofuran / 2.5 h / 40 °C

5: 83 percent / I₂; PPh₃; imidazole / CH₂Cl₂ / 3 h / 0 °C

6: 80 percent / NaHCO₃ / acetonitrile / 24 h / 65 °C

7: 46 percent / n-BuLi / hexane; tetrahydrofuran / 0.25 h / 0 °C

8: 61 percent / TMSBr / CH₂Cl₂ / 0.5 h / -30 °C

With 1H-imidazole; dmap; n-butyllithium; trimethylsilyl bromide; tetrabutyl ammonium fluoride; iodine; sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; hexane; dichloromethane; acetonitrile; 7: Wittig reaction;
DOI:10.1016/S0040-4020(01)00381-7

Reference yield:

: 358740-30-4
(3S,6E,10E)-tricosa-6,10-dien-1,3-diol

: 358740-37-1
(S)-3-[(9Z,15E,19E)-(2R,12S)-2-(tert-Butyl-diphenyl-silanyloxy)-12-hydroxy-dotriaconta-9,15,19-trienyl]-5-methyl-5H-furan-2-one

Guidance literature:: Multi-step reaction with 7 steps

1: i-Pr₂NEt; DMAP / CH₂Cl₂ / 18 h / 20 °C

2: 5.8 g / i-Pr₂NEt; DMAP / CH₂Cl₂ / 22 h / 20 °C

3: 94 percent / TBAF / tetrahydrofuran / 2.5 h / 40 °C

4: 83 percent / I₂; PPh₃; imidazole / CH₂Cl₂ / 3 h / 0 °C

5: 80 percent / NaHCO₃ / acetonitrile / 24 h / 65 °C

6: 46 percent / n-BuLi / hexane; tetrahydrofuran / 0.25 h / 0 °C

7: 61 percent / TMSBr / CH₂Cl₂ / 0.5 h / -30 °C

With 1H-imidazole; dmap; n-butyllithium; trimethylsilyl bromide; tetrabutyl ammonium fluoride; iodine; sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; hexane; dichloromethane; acetonitrile; 6: Wittig reaction;
DOI:10.1016/S0040-4020(01)00381-7