12,14-Nonadecadienal, 18-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-5,9-bis[(4-methoxyphenyl)meth oxy]-2,6-dimethyl-7-oxo-, (2R,5S,6S,9S,12E,14Z,18S)-

Base Information

Chemical Name:12,14-Nonadecadienal, 18-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-5,9-bis[(4-methoxyphenyl)meth oxy]-2,6-dimethyl-7-oxo-, (2R,5S,6S,9S,12E,14Z,18S)-
CAS No.:203387-54-6
Molecular Formula:C53H70O7Si
Molecular Weight:847.22
Hs Code.:

12,14-Nonadecadienal,
18-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-5,9-bis[(4-methoxyphenyl)meth
oxy]-2,6-dimethyl-7-oxo-, (2R,5S,6S,9S,12E,14Z,18S)-

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Chemical Property of 12,14-Nonadecadienal, 18-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-5,9-bis[(4-methoxyphenyl)meth oxy]-2,6-dimethyl-7-oxo-, (2R,5S,6S,9S,12E,14Z,18S)-

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Technology Process of 12,14-Nonadecadienal, 18-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-5,9-bis[(4-methoxyphenyl)meth oxy]-2,6-dimethyl-7-oxo-, (2R,5S,6S,9S,12E,14Z,18S)-

There total 44 articles about 12,14-Nonadecadienal, 18-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-5,9-bis[(4-methoxyphenyl)meth oxy]-2,6-dimethyl-7-oxo-, (2R,5S,6S,9S,12E,14Z,18S)- 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: 92.0%

: 668461-37-8
(2R,5S,6S,9S,12E,14Z,18S)-18-(tert-butyl(diphenyl)silyloxy)-2,6-dimethyl-5,9-di-(p-methoxybenzyloxy)-1-hydroxynonadeca-12,14-dien-7-one

: 203387-54-6
(2R,5S,6S,9S,12E,14Z,18S)-18-(tert-butyl(diphenyl)silyloxy)-2,6-dimethyl-5,9-di-(p-methoxybenzyloxy)-7-oxo-nonadeca-12,14-dienal

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; cooling;
DOI:10.1021/jo035391p

Reference yield:

: 203387-37-5
(5S)-5-(tert-butyl(diphenyl)silyloxy)-1-hexyne

: 203387-54-6
(2R,5S,6S,9S,12E,14Z,18S)-18-(tert-butyl(diphenyl)silyloxy)-2,6-dimethyl-5,9-di-(p-methoxybenzyloxy)-7-oxo-nonadeca-12,14-dienal

Guidance literature:: Multi-step reaction with 8 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 0.33 h / -78 °C

1.2: LiBr / tetrahydrofuran; hexane / 0.33 h / 20 °C

1.3: 89 percent / tetrahydrofuran; hexane / 2 h / -78 °C

2.1: propionic acid / xylene / 2 h / Heating

3.1: 94 percent / Zn; 1,2-dibromoethane; LiBr / CuBr / tetrahydrofuran / 2 h / Heating

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

5.1: (+)-chlorodiisopinocampheylborane; triethylamine / tetrahydrofuran / 0.5 h / -78 °C

5.2: tetrahydrofuran / 3 h / -90 °C

6.1: 83 percent / camphorsulfonic acid / cyclohexane; CH₂Cl₂ / 0 - 20 °C

7.1: 89 percent / DOWEX resin / tetrahydrofuran / 20 °C

8.1: 92 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / cooling

With n-butyllithium; oxalyl dichloride; Dowex resin; camphor-10-sulfonic acid; diisobutylaluminium hydride; dimethyl sulfoxide; propionic acid; ethylene dibromide; triethylamine; B-chlorodiisopinocampheylborane; lithium bromide; zinc; copper(I) bromide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; cyclohexane; toluene; xylene; 2.1: Johnson-Claisen rearrangement / 8.1: Swern oxidation;
DOI:10.1021/jo035391p

Reference yield:

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

: 203387-54-6
(2R,5S,6S,9S,12E,14Z,18S)-18-(tert-butyl(diphenyl)silyloxy)-2,6-dimethyl-5,9-di-(p-methoxybenzyloxy)-7-oxo-nonadeca-12,14-dienal

Guidance literature:: Multi-step reaction with 14 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: n-BuLi / tetrahydrofuran; hexane / 0.33 h / -78 °C

7.2: LiBr / tetrahydrofuran; hexane / 0.33 h / 20 °C

7.3: 89 percent / tetrahydrofuran; hexane / 2 h / -78 °C

8.1: propionic acid / xylene / 2 h / Heating

9.1: 94 percent / Zn; 1,2-dibromoethane; LiBr / CuBr / tetrahydrofuran / 2 h / Heating

10.1: 94 percent / DIBAL-H / diethyl ether; toluene / 2 h / -90 °C

11.1: (+)-chlorodiisopinocampheylborane; triethylamine / tetrahydrofuran / 0.5 h / -78 °C

11.2: tetrahydrofuran / 3 h / -90 °C

12.1: 83 percent / camphorsulfonic acid / cyclohexane; CH₂Cl₂ / 0 - 20 °C

13.1: 89 percent / DOWEX resin / tetrahydrofuran / 20 °C

14.1: 92 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / cooling

With n-butyllithium; oxalyl dichloride; Dowex resin; camphor-10-sulfonic acid; hydrogen; nickel; sodium hydride; diisobutylaluminium hydride; magnesium; dimethyl sulfoxide; propionic acid; ethylene dibromide; triethylamine; triphenylphosphine; B-chlorodiisopinocampheylborane; lithium bromide; zinc; copper(I) bromide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; cyclohexane; toluene; xylene; 2.1: Horner-Wadsworth-Simmons olefination / 8.1: Johnson-Claisen rearrangement / 14.1: Swern oxidation;
DOI:10.1021/jo035391p