(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

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
CAS No.:213408-84-5
Molecular Formula:C₆₂H₉₆O₉Si₂
Molecular Weight:1041.61
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

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

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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

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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

There total 26 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 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: 82.0%

: 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

: 213408-84-5
(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

Guidance literature:: With potassium hydroxide; In 1,4-dioxane; at 80 ℃; 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

: 213408-84-5
(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

Guidance literature:: Multi-step reaction with 10 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

10: 82 percent / aq. KOH / dioxane / 3 h / 80 °C

With dmap; manganese(IV) oxide; potassium hydroxide; 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; 1,4-dioxane; 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

: 213408-84-5
(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

Guidance literature:: Multi-step reaction with 13 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

13.1: 82 percent / aq. KOH / dioxane / 3 h / 80 °C

With pyridine; 2,6-dimethylpyridine; dmap; manganese(IV) oxide; potassium hydroxide; 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; 1,4-dioxane; 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