(2R,5S,6S,9S,12E,14Z,18S)-1-(tert-butyl(dimethyl)silyloxy)-18-(tert-butyl(diphenyl)silyloxy)-2,6-dimethyl-9-hydroxy-5-(p-methoxybenzyloxy)-7,7-(propan-1',3'-dithio)nonadeca-12,14-diene

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Chemical Name:(2R,5S,6S,9S,12E,14Z,18S)-1-(tert-butyl(dimethyl)silyloxy)-18-(tert-butyl(diphenyl)silyloxy)-2,6-dimethyl-9-hydroxy-5-(p-methoxybenzyloxy)-7,7-(propan-1',3'-dithio)nonadeca-12,14-diene
CAS No.:203387-50-2
Molecular Formula:C₅₄H₈₄O₅S₂Si₂
Molecular Weight:933.561
Hs Code.:

(2R,5S,6S,9S,12E,14Z,18S)-1-(tert-butyl(dimethyl)silyloxy)-18-(tert-butyl(diphenyl)silyloxy)-2,6-dimethyl-9-hydroxy-5-(p-methoxybenzyloxy)-7,7-(propan-1',3'-dithio)nonadeca-12,14-diene

Synonyms:(2R,5S,6S,9S,12E,14Z,18S)-1-(tert-butyl(dimethyl)silyloxy)-18-(tert-butyl(diphenyl)silyloxy)-2,6-dimethyl-9-hydroxy-5-(p-methoxybenzyloxy)-7,7-(propan-1',3'-dithio)nonadeca-12,14-diene

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Chemical Property of (2R,5S,6S,9S,12E,14Z,18S)-1-(tert-butyl(dimethyl)silyloxy)-18-(tert-butyl(diphenyl)silyloxy)-2,6-dimethyl-9-hydroxy-5-(p-methoxybenzyloxy)-7,7-(propan-1',3'-dithio)nonadeca-12,14-diene

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Technology Process of (2R,5S,6S,9S,12E,14Z,18S)-1-(tert-butyl(dimethyl)silyloxy)-18-(tert-butyl(diphenyl)silyloxy)-2,6-dimethyl-9-hydroxy-5-(p-methoxybenzyloxy)-7,7-(propan-1',3'-dithio)nonadeca-12,14-diene

There total 19 articles about (2R,5S,6S,9S,12E,14Z,18S)-1-(tert-butyl(dimethyl)silyloxy)-18-(tert-butyl(diphenyl)silyloxy)-2,6-dimethyl-9-hydroxy-5-(p-methoxybenzyloxy)-7,7-(propan-1',3'-dithio)nonadeca-12,14-diene 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: 40.0%

: 203387-48-8
tert-Butyl-((4Z,6E)-(S)-1-methyl-9-(S)-oxiranyl-nona-4,6-dienyloxy)-diphenyl-silane

: 203387-49-9
(2R,3S,6R)-7-(tert-butyl(dimethyl)silyloxy)-2,6-dimethyl-3-(p-methoxybenzyloxy)-1,1-(propan-1',3'-dithio)heptane

: 203387-50-2
(2R,5S,6S,9S,12E,14Z,18S)-1-(tert-butyl(dimethyl)silyloxy)-18-(tert-butyl(diphenyl)silyloxy)-2,6-dimethyl-9-hydroxy-5-(p-methoxybenzyloxy)-7,7-(propan-1',3'-dithio)nonadeca-12,14-diene

Guidance literature:: (2R,3S,6R)-7-(tert-butyl(dimethyl)silyloxy)-2,6-dimethyl-3-(p-methoxybenzyloxy)-1,1-(propan-1',3'-dithio)heptane; With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium; In tetrahydrofuran; hexane; at -60 - -40 ℃; for 2.25h;

tert-Butyl-((4Z,6E)-(S)-1-methyl-9-(S)-oxiranyl-nona-4,6-dienyloxy)-diphenyl-silane; In tetrahydrofuran; hexane; at -40 - 25 ℃;
DOI:10.1021/jo035391p

Reference yield:

: 87696-33-1
(S)-2-(O-tert-butyldiphenylsilyloxy)propanal

: 203387-50-2
(2R,5S,6S,9S,12E,14Z,18S)-1-(tert-butyl(dimethyl)silyloxy)-18-(tert-butyl(diphenyl)silyloxy)-2,6-dimethyl-9-hydroxy-5-(p-methoxybenzyloxy)-7,7-(propan-1',3'-dithio)nonadeca-12,14-diene

Guidance literature:: Multi-step reaction with 10 steps

1.1: NaH / tetrahydrofuran / 2 h

1.2: 75 percent / diethyl ether / 16 h / 22 °C

2.1: 83 percent / H₂; Raney nickel / methanol / 4500.36 Torr

3.1: 94 percent / DIBAL-H / diethyl ether; toluene / 2 h / -90 °C

4.1: triphenylphosphine; Zn / CH₂Cl₂ / 16 h / 20 °C

4.2: 75 percent / pyridine / CH₂Cl₂ / 2 h

5.1: 91 percent / Mg; 1,2-dibromoethane / tetrahydrofuran / Heating

6.1: 86 percent / butylamine; Pd(PPh₃)4; CuI / benzene / 12 h / 22 °C

7.1: 90 percent / Zn; 1,2-dibromoethane; LiBr / CuBr / tetrahydrofuran / 2 h / Heating

8.1: 73 percent / CF₃CO₂H / tetrahydrofuran; H₂O / 24 h / 20 °C

9.1: 66 percent / NaH; p-tosylimidazole / dimethylformamide / 1 h / -10 - 0 °C

10.1: s-BuLi; TMEDA; DMPU / tetrahydrofuran; hexane / 2.25 h / -60 - -40 °C

10.2: 40 percent / tetrahydrofuran; hexane / -40 - 25 °C

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; N,N,N,N,-tetramethylethylenediamine; hydrogen; sec.-butyllithium; nickel; sodium hydride; diisobutylaluminium hydride; magnesium; ethylene dibromide; N-butylamine; triphenylphosphine; N-tosylimidazole; trifluoroacetic acid; lithium bromide; zinc; copper(I) bromide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; benzene; 1.1: Horner-Wadsworth-Simmons olefination / 6.1: Castro-Sonogashira coupling;
DOI:10.1021/jo035391p

Reference yield:

: 102732-44-5
ethyl (S)-2-(tert-butyldiphenylsilyloxy)propanoate

: 203387-50-2
(2R,5S,6S,9S,12E,14Z,18S)-1-(tert-butyl(dimethyl)silyloxy)-18-(tert-butyl(diphenyl)silyloxy)-2,6-dimethyl-9-hydroxy-5-(p-methoxybenzyloxy)-7,7-(propan-1',3'-dithio)nonadeca-12,14-diene

Guidance literature:: Multi-step reaction with 11 steps

1.1: DIBAL-H / diethyl ether; toluene / 2 h / -90 °C

2.1: NaH / tetrahydrofuran / 2 h

2.2: 75 percent / diethyl ether / 16 h / 22 °C

3.1: 83 percent / H₂; Raney nickel / methanol / 4500.36 Torr

4.1: 94 percent / DIBAL-H / diethyl ether; toluene / 2 h / -90 °C

5.1: triphenylphosphine; Zn / CH₂Cl₂ / 16 h / 20 °C

5.2: 75 percent / pyridine / CH₂Cl₂ / 2 h

6.1: 91 percent / Mg; 1,2-dibromoethane / tetrahydrofuran / Heating

7.1: 86 percent / butylamine; Pd(PPh₃)4; CuI / benzene / 12 h / 22 °C

8.1: 90 percent / Zn; 1,2-dibromoethane; LiBr / CuBr / tetrahydrofuran / 2 h / Heating

9.1: 73 percent / CF₃CO₂H / tetrahydrofuran; H₂O / 24 h / 20 °C

10.1: 66 percent / NaH; p-tosylimidazole / dimethylformamide / 1 h / -10 - 0 °C

11.1: s-BuLi; TMEDA; DMPU / tetrahydrofuran; hexane / 2.25 h / -60 - -40 °C

11.2: 40 percent / tetrahydrofuran; hexane / -40 - 25 °C

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; N,N,N,N,-tetramethylethylenediamine; hydrogen; sec.-butyllithium; nickel; sodium hydride; diisobutylaluminium hydride; magnesium; ethylene dibromide; N-butylamine; triphenylphosphine; N-tosylimidazole; trifluoroacetic acid; lithium bromide; zinc; copper(I) bromide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; benzene; 2.1: Horner-Wadsworth-Simmons olefination / 7.1: Castro-Sonogashira coupling;
DOI:10.1021/jo035391p