(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

Base Information

Chemical Name:(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
CAS No.:668461-37-8
Molecular Formula:C₅₃H₇₂O₇Si
Molecular Weight:849.236
Hs Code.:

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 43 articles about (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 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%

: 668461-36-7
(2R,5S,6S,9S,12E,14Z,18S)-1-(tert-butyl(dimethyl)silyloxy)-18-(tert-butyl(diphenyl)silyloxy)-2,6-dimethyl-5,9-di-(p-methoxybenzyloxy)-nonadeca-12,14-dien-7-one

: 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

Guidance literature:: With Dowex resin; In tetrahydrofuran; at 20 ℃;
DOI:10.1021/jo035391p

Reference yield:

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

: 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

Guidance literature:: Multi-step reaction with 12 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: n-BuLi / tetrahydrofuran; hexane / 0.33 h / -78 °C

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

6.3: 89 percent / tetrahydrofuran; hexane / 2 h / -78 °C

7.1: propionic acid / xylene / 2 h / Heating

8.1: 94 percent / Zn; 1,2-dibromoethane; LiBr / CuBr / tetrahydrofuran / 2 h / Heating

9.1: 94 percent / DIBAL-H / diethyl ether; toluene / 2 h / -90 °C

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

10.2: tetrahydrofuran / 3 h / -90 °C

11.1: 83 percent / camphorsulfonic acid / cyclohexane; CH₂Cl₂ / 0 - 20 °C

12.1: 89 percent / DOWEX resin / tetrahydrofuran / 20 °C

With n-butyllithium; Dowex resin; camphor-10-sulfonic acid; hydrogen; nickel; sodium hydride; diisobutylaluminium hydride; magnesium; propionic acid; ethylene dibromide; triethylamine; triphenylphosphine; B-chlorodiisopinocampheylborane; lithium bromide; zinc; copper(I) bromide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; cyclohexane; toluene; xylene; 1.1: Horner-Wadsworth-Simmons olefination / 7.1: Johnson-Claisen rearrangement;
DOI:10.1021/jo035391p

Reference yield:

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

: 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

Guidance literature:: Multi-step reaction with 7 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

With n-butyllithium; Dowex resin; camphor-10-sulfonic acid; diisobutylaluminium hydride; 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;
DOI:10.1021/jo035391p