(2Z,4E,12E,14E)-(6R,7R,8S,9S,10R,16S,17R,18S)-7,9-Bis-(diethyl-isopropyl-silanyloxy)-8-ethyl-17-hydroxy-2,16-dimethoxy-19-[(4-methoxy-phenyl)-diphenyl-methoxy]-4,6,10,12,18-pentamethyl-nonadeca-2,4,12,14-tetraenoic acid methyl ester

Base Information

Chemical Name:(2Z,4E,12E,14E)-(6R,7R,8S,9S,10R,16S,17R,18S)-7,9-Bis-(diethyl-isopropyl-silanyloxy)-8-ethyl-17-hydroxy-2,16-dimethoxy-19-[(4-methoxy-phenyl)-diphenyl-methoxy]-4,6,10,12,18-pentamethyl-nonadeca-2,4,12,14-tetraenoic acid methyl ester
CAS No.:213408-83-4
Molecular Formula:C₆₃H₉₈O₉Si₂
Molecular Weight:1055.64
Hs Code.:

(2Z,4E,12E,14E)-(6R,7R,8S,9S,10R,16S,17R,18S)-7,9-Bis-(diethyl-isopropyl-silanyloxy)-8-ethyl-17-hydroxy-2,16-dimethoxy-19-[(4-methoxy-phenyl)-diphenyl-methoxy]-4,6,10,12,18-pentamethyl-nonadeca-2,4,12,14-tetraenoic acid methyl ester

Synonyms:(2Z,4E,12E,14E)-(6R,7R,8S,9S,10R,16S,17R,18S)-7,9-Bis-(diethyl-isopropyl-silanyloxy)-8-ethyl-17-hydroxy-2,16-dimethoxy-19-[(4-methoxy-phenyl)-diphenyl-methoxy]-4,6,10,12,18-pentamethyl-nonadeca-2,4,12,14-tetraenoic acid methyl ester

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Chemical Property of (2Z,4E,12E,14E)-(6R,7R,8S,9S,10R,16S,17R,18S)-7,9-Bis-(diethyl-isopropyl-silanyloxy)-8-ethyl-17-hydroxy-2,16-dimethoxy-19-[(4-methoxy-phenyl)-diphenyl-methoxy]-4,6,10,12,18-pentamethyl-nonadeca-2,4,12,14-tetraenoic acid methyl ester

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Technology Process of (2Z,4E,12E,14E)-(6R,7R,8S,9S,10R,16S,17R,18S)-7,9-Bis-(diethyl-isopropyl-silanyloxy)-8-ethyl-17-hydroxy-2,16-dimethoxy-19-[(4-methoxy-phenyl)-diphenyl-methoxy]-4,6,10,12,18-pentamethyl-nonadeca-2,4,12,14-tetraenoic acid methyl ester

There total 25 articles about (2Z,4E,12E,14E)-(6R,7R,8S,9S,10R,16S,17R,18S)-7,9-Bis-(diethyl-isopropyl-silanyloxy)-8-ethyl-17-hydroxy-2,16-dimethoxy-19-[(4-methoxy-phenyl)-diphenyl-methoxy]-4,6,10,12,18-pentamethyl-nonadeca-2,4,12,14-tetraenoic 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: 100.0%

: 14470-28-1
mono-4-methoxytrityl chloride

: 213408-82-3
(2Z,4E,12E,14E)-(6R,7R,8S,9S,10R,16S,17R,18S)-7,9-Bis-(diethyl-isopropyl-silanyloxy)-8-ethyl-17,19-dihydroxy-2,16-dimethoxy-4,6,10,12,18-pentamethyl-nonadeca-2,4,12,14-tetraenoic acid methyl ester

: 213408-83-4
(2Z,4E,12E,14E)-(6R,7R,8S,9S,10R,16S,17R,18S)-7,9-Bis-(diethyl-isopropyl-silanyloxy)-8-ethyl-17-hydroxy-2,16-dimethoxy-19-[(4-methoxy-phenyl)-diphenyl-methoxy]-4,6,10,12,18-pentamethyl-nonadeca-2,4,12,14-tetraenoic acid methyl ester

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 25 ℃; for 3h;
DOI:10.1021/jo001377q

Reference yield:

: 213402-11-0
2,2-Dimethyl-propionic acid (E)-(2R,3R,4S,5S,6R)-3,5-bis-(diethyl-isopropyl-silanyloxy)-4-ethyl-9-iodo-2,6,8-trimethyl-non-8-enyl ester

: 213408-83-4
(2Z,4E,12E,14E)-(6R,7R,8S,9S,10R,16S,17R,18S)-7,9-Bis-(diethyl-isopropyl-silanyloxy)-8-ethyl-17-hydroxy-2,16-dimethoxy-19-[(4-methoxy-phenyl)-diphenyl-methoxy]-4,6,10,12,18-pentamethyl-nonadeca-2,4,12,14-tetraenoic acid methyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 72 percent / triphenylarsine; LiCl / tris(dibenzylideneacetone)dipalladium / 1-methyl-pyrrolidin-2-one / 16 h / 40 °C

2: 96 percent / methyllithium / diethyl ether / 0.5 h / 25 °C

3: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 0.33 h / -78 °C

4: 0.597 g / toluene / 16 h / 100 °C

5: 90 percent / diisobutylaluminum hydride / toluene / 0.5 h / -78 °C

6: 100 percent / MnO₂ / CH₂Cl₂ / 1.5 h / 25 °C

7: 99 percent / potassium bis(trimethylsilyl)amide; 18-crown-6-ether / tetrahydrofuran; toluene / 16 h / -20 °C

8: 96 percent / pyridinium p-toluenesulfonate / methanol / 1 h / 25 °C

9: 100 percent / Et₃N; 4-(dimethylamino)pyridine / CH₂Cl₂ / 3 h / 25 °C

With dmap; manganese(IV) oxide; oxalyl dichloride; 18-crown-6 ether; triphenyl-arsane; methyllithium; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; lithium chloride; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; methanol; diethyl ether; dichloromethane; toluene; 1: Stille coupling / 3: Swern oxidation / 4: Wittig reaction / 7: Horner-Wadsworth-Emmons reaction;
DOI:10.1021/jo001377q

Reference yield:

: 213402-94-9
(2R,3R,4S,5S,6R)-4-Ethyl-2,6-dimethyl-non-8-yne-1,3,5-triol

: 213408-83-4
(2Z,4E,12E,14E)-(6R,7R,8S,9S,10R,16S,17R,18S)-7,9-Bis-(diethyl-isopropyl-silanyloxy)-8-ethyl-17-hydroxy-2,16-dimethoxy-19-[(4-methoxy-phenyl)-diphenyl-methoxy]-4,6,10,12,18-pentamethyl-nonadeca-2,4,12,14-tetraenoic acid methyl ester

Guidance literature:: Multi-step reaction with 12 steps

1.1: 83 percent / pyridine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 16 h / 25 °C

2.1: 99 percent / 2,6-lutidine / CH₂Cl₂ / 4 h / 25 °C

3.1: Cp₂ZrCl₂ / 1,2-dichloro-ethane; hexane / 16 h / 25 °C

3.2: 88 percent / I₂ / tetrahydrofuran; 1,2-dichloro-ethane; hexane / 1.5 h / -30 °C

4.1: 72 percent / triphenylarsine; LiCl / tris(dibenzylideneacetone)dipalladium / 1-methyl-pyrrolidin-2-one / 16 h / 40 °C

5.1: 96 percent / methyllithium / diethyl ether / 0.5 h / 25 °C

6.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 0.33 h / -78 °C

7.1: 0.597 g / toluene / 16 h / 100 °C

8.1: 90 percent / diisobutylaluminum hydride / toluene / 0.5 h / -78 °C

9.1: 100 percent / MnO₂ / CH₂Cl₂ / 1.5 h / 25 °C

10.1: 99 percent / potassium bis(trimethylsilyl)amide; 18-crown-6-ether / tetrahydrofuran; toluene / 16 h / -20 °C

11.1: 96 percent / pyridinium p-toluenesulfonate / methanol / 1 h / 25 °C

12.1: 100 percent / Et₃N; 4-(dimethylamino)pyridine / CH₂Cl₂ / 3 h / 25 °C

With pyridine; 2,6-dimethylpyridine; dmap; manganese(IV) oxide; oxalyl dichloride; 18-crown-6 ether; triphenyl-arsane; methyllithium; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; lithium chloride; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; zirconocene dichloride; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; methanol; diethyl ether; hexane; dichloromethane; 1,2-dichloro-ethane; toluene; 4.1: Stille coupling / 6.1: Swern oxidation / 7.1: Wittig reaction / 10.1: Horner-Wadsworth-Emmons reaction;
DOI:10.1021/jo001377q