(2E,4E,6E,10E,12E)-(8R,9R,16S,17S,19S)-20-Benzyloxy-16,19-bis-(tert-butyl-dimethyl-silanyloxy)-9-hydroxy-17-methoxy-2,4,6,8,12-pentamethyl-icosa-2,4,6,10,12-pentaenoic acid 2-trimethylsilanyl-ethyl ester

Base Information

Chemical Name:(2E,4E,6E,10E,12E)-(8R,9R,16S,17S,19S)-20-Benzyloxy-16,19-bis-(tert-butyl-dimethyl-silanyloxy)-9-hydroxy-17-methoxy-2,4,6,8,12-pentamethyl-icosa-2,4,6,10,12-pentaenoic acid 2-trimethylsilanyl-ethyl ester
CAS No.:268736-80-7
Molecular Formula:C₅₀H₈₈O₇Si₃
Molecular Weight:885.501
Hs Code.:

(2E,4E,6E,10E,12E)-(8R,9R,16S,17S,19S)-20-Benzyloxy-16,19-bis-(tert-butyl-dimethyl-silanyloxy)-9-hydroxy-17-methoxy-2,4,6,8,12-pentamethyl-icosa-2,4,6,10,12-pentaenoic acid 2-trimethylsilanyl-ethyl ester

Synonyms:(2E,4E,6E,10E,12E)-(8R,9R,16S,17S,19S)-20-Benzyloxy-16,19-bis-(tert-butyl-dimethyl-silanyloxy)-9-hydroxy-17-methoxy-2,4,6,8,12-pentamethyl-icosa-2,4,6,10,12-pentaenoic acid 2-trimethylsilanyl-ethyl ester

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Chemical Property of (2E,4E,6E,10E,12E)-(8R,9R,16S,17S,19S)-20-Benzyloxy-16,19-bis-(tert-butyl-dimethyl-silanyloxy)-9-hydroxy-17-methoxy-2,4,6,8,12-pentamethyl-icosa-2,4,6,10,12-pentaenoic acid 2-trimethylsilanyl-ethyl ester

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Technology Process of (2E,4E,6E,10E,12E)-(8R,9R,16S,17S,19S)-20-Benzyloxy-16,19-bis-(tert-butyl-dimethyl-silanyloxy)-9-hydroxy-17-methoxy-2,4,6,8,12-pentamethyl-icosa-2,4,6,10,12-pentaenoic acid 2-trimethylsilanyl-ethyl ester

There total 16 articles about (2E,4E,6E,10E,12E)-(8R,9R,16S,17S,19S)-20-Benzyloxy-16,19-bis-(tert-butyl-dimethyl-silanyloxy)-9-hydroxy-17-methoxy-2,4,6,8,12-pentamethyl-icosa-2,4,6,10,12-pentaenoic acid 2-trimethylsilanyl-ethyl 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: 60.0%

: 268736-69-2
(2E,4E,6E)-(8R,9S)-9-Hydroxy-2,4,6,8-tetramethyl-undeca-2,4,6-trien-10-ynoic acid 2-trimethylsilanyl-ethyl ester

: 268736-58-9
[(E)-(2S,4S,5S)-2,5-Bis-(tert-butyl-dimethyl-silanyloxy)-9-iodo-4-methoxy-dec-8-enyloxymethyl]-benzene

: 268736-80-7
(2E,4E,6E,10E,12E)-(8R,9R,16S,17S,19S)-20-Benzyloxy-16,19-bis-(tert-butyl-dimethyl-silanyloxy)-9-hydroxy-17-methoxy-2,4,6,8,12-pentamethyl-icosa-2,4,6,10,12-pentaenoic acid 2-trimethylsilanyl-ethyl ester

Guidance literature:: (2E,4E,6E)-(8R,9S)-9-Hydroxy-2,4,6,8-tetramethyl-undeca-2,4,6-trien-10-ynoic acid 2-trimethylsilanyl-ethyl ester; With Bu₃Sn; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; at 0 ℃; for 0.5h;

[(E)-(2S,4S,5S)-2,5-Bis-(tert-butyl-dimethyl-silanyloxy)-9-iodo-4-methoxy-dec-8-enyloxymethyl]-benzene; dichloro bis(acetonitrile) palladium(II); In N,N-dimethyl-formamide; at 25 ℃; for 48h; Further stages.;
DOI:10.1039/b000424n

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 268736-80-7
(2E,4E,6E,10E,12E)-(8R,9R,16S,17S,19S)-20-Benzyloxy-16,19-bis-(tert-butyl-dimethyl-silanyloxy)-9-hydroxy-17-methoxy-2,4,6,8,12-pentamethyl-icosa-2,4,6,10,12-pentaenoic acid 2-trimethylsilanyl-ethyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: 97 percent / 2,6-Lutidine / CH₂Cl₂ / 0 - 25 °C

2.1: Cp₂ZrHCl / tetrahydrofuran / 2 h / 50 °C

2.2: I₂ / tetrahydrofuran / 0.5 h / -15 - 25 °C

3.1: Bu₃Sn / PdCl₂(PPh₃)2 / tetrahydrofuran / 0.5 h / 0 °C

3.2: 60 percent / Pd(CH₃CN)2Cl₂ / dimethylformamide / 48 h / 25 °C

With 2,6-dimethylpyridine; Schwartz's reagent; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; dichloromethane; 1.1: Etherification / 2.1: Metallation / 2.2: Iodination / 3.1: Addition / 3.2: Alkylation;
DOI:10.1039/b000424n

Reference yield:

: 100-39-0
benzyl bromide

: 268736-80-7
(2E,4E,6E,10E,12E)-(8R,9R,16S,17S,19S)-20-Benzyloxy-16,19-bis-(tert-butyl-dimethyl-silanyloxy)-9-hydroxy-17-methoxy-2,4,6,8,12-pentamethyl-icosa-2,4,6,10,12-pentaenoic acid 2-trimethylsilanyl-ethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: Bu₂SnO / toluene / 12 h / 110 °C

1.2: 85 percent / Bu₄NI / toluene / 2 h / 80 °C

2.1: 97 percent / 2,6-Lutidine / CH₂Cl₂ / 0 - 25 °C

3.1: Cp₂ZrHCl / tetrahydrofuran / 2 h / 50 °C

3.2: I₂ / tetrahydrofuran / 0.5 h / -15 - 25 °C

4.1: Bu₃Sn / PdCl₂(PPh₃)2 / tetrahydrofuran / 0.5 h / 0 °C

4.2: 60 percent / Pd(CH₃CN)2Cl₂ / dimethylformamide / 48 h / 25 °C

With 2,6-dimethylpyridine; Schwartz's reagent; di(n-butyl)tin oxide; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; dichloromethane; toluene; 1.1: Substitution / 1.2: Etherification / 2.1: Etherification / 3.1: Metallation / 3.2: Iodination / 4.1: Addition / 4.2: Alkylation;
DOI:10.1039/b000424n