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

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Chemical Name:(E)-(S)-4-[(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-1-(4-methoxy-phenyl)-4-oxo-azetidin-2-yl]-pent-2-enoic acid ethyl ester
CAS No.:171782-13-1
Molecular Formula:C₂₅H₃₉NO₅Si
Molecular Weight:461.674
Hs Code.:

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

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

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

There total 5 articles about (E)-(S)-4-[(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-1-(4-methoxy-phenyl)-4-oxo-azetidin-2-yl]-pent-2-enoic 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: 87.0%

: 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

: 171782-13-1
(E)-(S)-4-[(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-1-(4-methoxy-phenyl)-4-oxo-azetidin-2-yl]-pent-2-enoic acid ethyl ester

Guidance literature:: With palladium diacetate; formic acid; triphenylphosphine; In 1,4-dioxane; at 90 ℃; for 10h;
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

: 171782-13-1
(E)-(S)-4-[(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-1-(4-methoxy-phenyl)-4-oxo-azetidin-2-yl]-pent-2-enoic 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: 87 percent / HCOOH, Pd(OAc)2, PPh₃ / dioxane / 10 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

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 171782-13-1
(E)-(S)-4-[(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-1-(4-methoxy-phenyl)-4-oxo-azetidin-2-yl]-pent-2-enoic acid ethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: imidazole / dimethylformamide / Ambient temperature

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

3: 99 percent / 4-N,N-dimethylaminopyridine / CH₂Cl₂ / 13 h

4: 87 percent / HCOOH, Pd(OAc)2, PPh₃ / dioxane / 10 h / 90 °C

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