(E)-4-[(2S,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-1-(4-methoxy-phenyl)-4-oxo-azetidin-2-yl]-penta-2,4-dienoic acid ethyl ester

Base Information

Chemical Name:(E)-4-[(2S,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-1-(4-methoxy-phenyl)-4-oxo-azetidin-2-yl]-penta-2,4-dienoic acid ethyl ester
CAS No.:171782-15-3
Molecular Formula:C₂₅H₃₇NO₅Si
Molecular Weight:459.658
Hs Code.:

Synonyms:(E)-4-[(2S,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-1-(4-methoxy-phenyl)-4-oxo-azetidin-2-yl]-penta-2,4-dienoic acid ethyl ester

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (E)-4-[(2S,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-1-(4-methoxy-phenyl)-4-oxo-azetidin-2-yl]-penta-2,4-dienoic acid ethyl ester

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of (E)-4-[(2S,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-1-(4-methoxy-phenyl)-4-oxo-azetidin-2-yl]-penta-2,4-dienoic acid ethyl ester

There total 8 articles about (E)-4-[(2S,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-1-(4-methoxy-phenyl)-4-oxo-azetidin-2-yl]-penta-2,4-dienoic acid 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: 98.0%

: 207291-30-3
4-Acetoxy-4-[(2S,3S)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1-(4-methoxy-phenyl)-4-oxo-azetidin-2-yl]-pent-2-ynoic acid ethyl ester

: 171782-15-3
(E)-4-[(2S,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-1-(4-methoxy-phenyl)-4-oxo-azetidin-2-yl]-penta-2,4-dienoic acid ethyl ester

Guidance literature:: With palladium diacetate; formic acid; triphenylphosphine; In 1,4-dioxane; at 90 ℃; for 22h;
DOI:10.1246/cl.1995.1013

Reference yield:

: 104401-80-1
(3S,4S)-4-Acetyl-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1-(4-methoxy-phenyl)-azetidin-2-one

: 171782-15-3
(E)-4-[(2S,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-1-(4-methoxy-phenyl)-4-oxo-azetidin-2-yl]-penta-2,4-dienoic acid ethyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 1.) LDA / 1.) THF, from -78 to -40 deg C, 1.5 h

2: 99 percent / 4-N,N-dimethylaminopyridine / CH₂Cl₂ / 13 h

3: 98 percent / HCOOH, Pd(OAc)2, PPh₃ / dioxane / 22 h / 90 °C

With dmap; palladium diacetate; formic acid; triphenylphosphine; lithium diisopropyl amide; In 1,4-dioxane; dichloromethane;
DOI:10.1246/cl.1995.1013

Reference yield:

: 139308-11-5
(4S)-4-<(4S,5S)-4,5-dimethoxymethyl-2-methyl-1,3-dioxolan-2-yl>-1-p-methoxyphenyl-2-azetidinone

: 171782-15-3
(E)-4-[(2S,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-1-(4-methoxy-phenyl)-4-oxo-azetidin-2-yl]-penta-2,4-dienoic acid ethyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 2.) DIBAL

2: 97 percent / CF₃SO₃H / butan-2-one

3: imidazole / dimethylformamide / Ambient temperature

4: 1.) LDA / 1.) THF, from -78 to -40 deg C, 1.5 h

5: 99 percent / 4-N,N-dimethylaminopyridine / CH₂Cl₂ / 13 h

6: 98 percent / HCOOH, Pd(OAc)2, PPh₃ / dioxane / 22 h / 90 °C

With 1H-imidazole; dmap; palladium diacetate; formic acid; trifluorormethanesulfonic acid; diisobutylaluminium hydride; triphenylphosphine; lithium diisopropyl amide; In 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide; butanone;
DOI:10.1246/cl.1995.1013