2-(trimethylsilyl)ethyl (2E,4Z,6E,8R,9S,2'S,3'S)-8-(2'-acetylamino-3'-phenylbutanoyloxy)-9,10-epoxy-9-methyldeca-2,4,6-trienoate

Base Information

Chemical Name:2-(trimethylsilyl)ethyl (2E,4Z,6E,8R,9S,2'S,3'S)-8-(2'-acetylamino-3'-phenylbutanoyloxy)-9,10-epoxy-9-methyldeca-2,4,6-trienoate
CAS No.:439808-15-8
Molecular Formula:C₂₈H₃₉NO₆Si
Molecular Weight:513.706
Hs Code.:

Synonyms:2-(trimethylsilyl)ethyl (2E,4Z,6E,8R,9S,2'S,3'S)-8-(2'-acetylamino-3'-phenylbutanoyloxy)-9,10-epoxy-9-methyldeca-2,4,6-trienoate

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Chemical Property of 2-(trimethylsilyl)ethyl (2E,4Z,6E,8R,9S,2'S,3'S)-8-(2'-acetylamino-3'-phenylbutanoyloxy)-9,10-epoxy-9-methyldeca-2,4,6-trienoate

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Technology Process of 2-(trimethylsilyl)ethyl (2E,4Z,6E,8R,9S,2'S,3'S)-8-(2'-acetylamino-3'-phenylbutanoyloxy)-9,10-epoxy-9-methyldeca-2,4,6-trienoate

There total 8 articles about 2-(trimethylsilyl)ethyl (2E,4Z,6E,8R,9S,2'S,3'S)-8-(2'-acetylamino-3'-phenylbutanoyloxy)-9,10-epoxy-9-methyldeca-2,4,6-trienoate 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:

: 356787-10-5
(2R,3S)-2-(tert-butyldiphenylsilyl)oxy-3,4-epoxy-3-methylbutanal

: 439808-15-8
2-(trimethylsilyl)ethyl (2E,4Z,6E,8R,9S,2'S,3'S)-8-(2'-acetylamino-3'-phenylbutanoyloxy)-9,10-epoxy-9-methyldeca-2,4,6-trienoate

Guidance literature:: Multi-step reaction with 8 steps

1.1: LiCl; N,N-diisopropylethylamine / acetonitrile / 0.5 h / 20 °C

1.2: 54 percent / acetonitrile / 20 °C

2.1: 92 percent / CH₂Cl₂ / 1 h / -20 °C

3.1: 89 percent / triphenylphosphine; tributyltin hydride / palladium acetate / benzene / 2 h / 20 °C

4.1: 85 percent / tetrabutylammonium fluoride / tetrahydrofuran / 20 °C

5.1: 51 percent / dichlorobis(triphenylphosphine)palladium / dimethylformamide / 5.5 h / 50 °C

6.1: 1,3-dicyclohexylcarbodiimide; 4-pyrrolidinopyridine / ethyl acetate / 1 h / 20 °C

7.1: piperidine / CH₂Cl₂ / 5 h / 20 °C

8.1: 657 mg / pyridine / CH₂Cl₂ / 0.5 h / 20 °C

With piperidine; pyridine; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; 4-pyrrolidin-1-ylpyridine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; triphenylphosphine; lithium chloride; bis-triphenylphosphine-palladium(II) chloride; palladium diacetate; In tetrahydrofuran; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; benzene; 1.2: Horner-Wadsworth-Emmons reaction / 5.1: Stille coupling;
DOI:10.1016/S0040-4020(02)00117-5

Reference yield:

: 439808-10-3
(4E,6Z,2S,3R)-7-bromo-1,2-epoxy-2-methylhepta-4,6-dien-3-ol

: 439808-15-8
2-(trimethylsilyl)ethyl (2E,4Z,6E,8R,9S,2'S,3'S)-8-(2'-acetylamino-3'-phenylbutanoyloxy)-9,10-epoxy-9-methyldeca-2,4,6-trienoate

Guidance literature:: Multi-step reaction with 4 steps

1: 51 percent / dichlorobis(triphenylphosphine)palladium / dimethylformamide / 5.5 h / 50 °C

2: 1,3-dicyclohexylcarbodiimide; 4-pyrrolidinopyridine / ethyl acetate / 1 h / 20 °C

3: piperidine / CH₂Cl₂ / 5 h / 20 °C

4: 657 mg / pyridine / CH₂Cl₂ / 0.5 h / 20 °C

With piperidine; pyridine; 4-pyrrolidin-1-ylpyridine; dicyclohexyl-carbodiimide; bis-triphenylphosphine-palladium(II) chloride; In dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 1: Stille coupling;
DOI:10.1016/S0040-4020(02)00117-5

Reference yield:

: 439808-07-8
(2E,4R,5S)-4-(tert-butyldiphenylsilyl)oxy-5,6-epoxy-5-methylhex-2-enal

: 439808-15-8
2-(trimethylsilyl)ethyl (2E,4Z,6E,8R,9S,2'S,3'S)-8-(2'-acetylamino-3'-phenylbutanoyloxy)-9,10-epoxy-9-methyldeca-2,4,6-trienoate

Guidance literature:: Multi-step reaction with 7 steps

1: 92 percent / CH₂Cl₂ / 1 h / -20 °C

2: 89 percent / triphenylphosphine; tributyltin hydride / palladium acetate / benzene / 2 h / 20 °C

3: 85 percent / tetrabutylammonium fluoride / tetrahydrofuran / 20 °C

4: 51 percent / dichlorobis(triphenylphosphine)palladium / dimethylformamide / 5.5 h / 50 °C

5: 1,3-dicyclohexylcarbodiimide; 4-pyrrolidinopyridine / ethyl acetate / 1 h / 20 °C

6: piperidine / CH₂Cl₂ / 5 h / 20 °C

7: 657 mg / pyridine / CH₂Cl₂ / 0.5 h / 20 °C

With piperidine; pyridine; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; 4-pyrrolidin-1-ylpyridine; dicyclohexyl-carbodiimide; triphenylphosphine; bis-triphenylphosphine-palladium(II) chloride; palladium diacetate; In tetrahydrofuran; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; benzene; 4: Stille coupling;
DOI:10.1016/S0040-4020(02)00117-5