(3Z,5E,13E,15E)-(7R,8R,9S,10S,11R,17S,18R)-8,10-Bis-(diethyl-isopropyl-silanyloxy)-9-ethyl-3,17-dimethoxy-18-{(S)-2-[(4-methoxy-phenyl)-diphenyl-methoxy]-1-methyl-ethyl}-5,7,11,13-tetramethyl-oxacyclooctadeca-3,5,13,15-tetraen-2-one

Base Information

Chemical Name:(3Z,5E,13E,15E)-(7R,8R,9S,10S,11R,17S,18R)-8,10-Bis-(diethyl-isopropyl-silanyloxy)-9-ethyl-3,17-dimethoxy-18-{(S)-2-[(4-methoxy-phenyl)-diphenyl-methoxy]-1-methyl-ethyl}-5,7,11,13-tetramethyl-oxacyclooctadeca-3,5,13,15-tetraen-2-one
CAS No.:213408-85-6
Molecular Formula:C₆₂H₉₄O₈Si₂
Molecular Weight:1023.59
Hs Code.:

(3Z,5E,13E,15E)-(7R,8R,9S,10S,11R,17S,18R)-8,10-Bis-(diethyl-isopropyl-silanyloxy)-9-ethyl-3,17-dimethoxy-18-{(S)-2-[(4-methoxy-phenyl)-diphenyl-methoxy]-1-methyl-ethyl}-5,7,11,13-tetramethyl-oxacyclooctadeca-3,5,13,15-tetraen-2-one

Synonyms:(3Z,5E,13E,15E)-(7R,8R,9S,10S,11R,17S,18R)-8,10-Bis-(diethyl-isopropyl-silanyloxy)-9-ethyl-3,17-dimethoxy-18-{(S)-2-[(4-methoxy-phenyl)-diphenyl-methoxy]-1-methyl-ethyl}-5,7,11,13-tetramethyl-oxacyclooctadeca-3,5,13,15-tetraen-2-one

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Chemical Property of (3Z,5E,13E,15E)-(7R,8R,9S,10S,11R,17S,18R)-8,10-Bis-(diethyl-isopropyl-silanyloxy)-9-ethyl-3,17-dimethoxy-18-{(S)-2-[(4-methoxy-phenyl)-diphenyl-methoxy]-1-methyl-ethyl}-5,7,11,13-tetramethyl-oxacyclooctadeca-3,5,13,15-tetraen-2-one

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Technology Process of (3Z,5E,13E,15E)-(7R,8R,9S,10S,11R,17S,18R)-8,10-Bis-(diethyl-isopropyl-silanyloxy)-9-ethyl-3,17-dimethoxy-18-{(S)-2-[(4-methoxy-phenyl)-diphenyl-methoxy]-1-methyl-ethyl}-5,7,11,13-tetramethyl-oxacyclooctadeca-3,5,13,15-tetraen-2-one

There total 36 articles about (3Z,5E,13E,15E)-(7R,8R,9S,10S,11R,17S,18R)-8,10-Bis-(diethyl-isopropyl-silanyloxy)-9-ethyl-3,17-dimethoxy-18-{(S)-2-[(4-methoxy-phenyl)-diphenyl-methoxy]-1-methyl-ethyl}-5,7,11,13-tetramethyl-oxacyclooctadeca-3,5,13,15-tetraen-2-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: 82.0%

: 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

: 213408-85-6
(3Z,5E,13E,15E)-(7R,8R,9S,10S,11R,17S,18R)-8,10-Bis-(diethyl-isopropyl-silanyloxy)-9-ethyl-3,17-dimethoxy-18-{(S)-2-[(4-methoxy-phenyl)-diphenyl-methoxy]-1-methyl-ethyl}-5,7,11,13-tetramethyl-oxacyclooctadeca-3,5,13,15-tetraen-2-one

Guidance literature:: With dmap; 2,4,6-trichlorobenzoyl chloride; triethylamine; In tetrahydrofuran; toluene; at 110 ℃; for 14h;
DOI:10.1016/S0040-4039(98)01234-9

Reference yield: 72.0%

: 7,9-bis-(diethyl-isopropyl-silanyloxy)-8-ethyl-13-iodo-2-methoxy-4,6,10,12-tetramethyl-trideca-2,4,12-trienoic acid 2-methoxy-1-{2-[(4-methoxy-phenyl)-diphenyl-methoxy]-1-methyl-ethyl}-4-tributylstannanyl-but-3-enyl ester

: 213408-85-6
(3Z,5E,13E,15E)-(7R,8R,9S,10S,11R,17S,18R)-8,10-Bis-(diethyl-isopropyl-silanyloxy)-9-ethyl-3,17-dimethoxy-18-{(S)-2-[(4-methoxy-phenyl)-diphenyl-methoxy]-1-methyl-ethyl}-5,7,11,13-tetramethyl-oxacyclooctadeca-3,5,13,15-tetraen-2-one

Guidance literature:: With triphenyl-arsane; N-ethyl-N,N-diisopropylamine; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; In tetrahydrofuran; N,N-dimethyl-formamide; at 60 ℃; for 18h;
DOI:10.1021/jo001377q

Reference yield:

: 213403-07-7
2,2-Dimethyl-propionic acid (2R,3R,4S,5S,6R)-3,5-bis-(diethyl-isopropyl-silanyloxy)-4-ethyl-2,6-dimethyl-non-8-ynyl ester

: 213408-85-6
(3Z,5E,13E,15E)-(7R,8R,9S,10S,11R,17S,18R)-8,10-Bis-(diethyl-isopropyl-silanyloxy)-9-ethyl-3,17-dimethoxy-18-{(S)-2-[(4-methoxy-phenyl)-diphenyl-methoxy]-1-methyl-ethyl}-5,7,11,13-tetramethyl-oxacyclooctadeca-3,5,13,15-tetraen-2-one

Guidance literature:: Multi-step reaction with 12 steps

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

1.2: 88 percent / I₂ / tetrahydrofuran; 1,2-dichloro-ethane; hexane / 1.5 h / -30 °C

2.1: 72 percent / triphenylarsine; LiCl / tris(dibenzylideneacetone)dipalladium / 1-methyl-pyrrolidin-2-one / 16 h / 40 °C

3.1: 96 percent / methyllithium / diethyl ether / 0.5 h / 25 °C

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

5.1: 0.597 g / toluene / 16 h / 100 °C

6.1: 90 percent / diisobutylaluminum hydride / toluene / 0.5 h / -78 °C

7.1: 100 percent / MnO₂ / CH₂Cl₂ / 1.5 h / 25 °C

8.1: 99 percent / potassium bis(trimethylsilyl)amide; 18-crown-6-ether / tetrahydrofuran; toluene / 16 h / -20 °C

9.1: 96 percent / pyridinium p-toluenesulfonate / methanol / 1 h / 25 °C

10.1: 100 percent / Et₃N; 4-(dimethylamino)pyridine / CH₂Cl₂ / 3 h / 25 °C

11.1: 82 percent / aq. KOH / dioxane / 3 h / 80 °C

12.1: 2,4,6-trichlorobenzoyl chloride; Et₃N / tetrahydrofuran / 3 h / 25 °C

12.2: 82 percent / 4-(dimethylamino)pyridine / tetrahydrofuran; toluene / 14 h / 110 °C

With dmap; manganese(IV) oxide; potassium hydroxide; oxalyl dichloride; 18-crown-6 ether; triphenyl-arsane; 2,4,6-trichlorobenzoyl chloride; 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; 2.1: Stille coupling / 4.1: Swern oxidation / 5.1: Wittig reaction / 8.1: Horner-Wadsworth-Emmons reaction / 12.1: Yamaguchi macrolactonization / 12.2: Yamaguchi macrolactonization;
DOI:10.1021/jo001377q