Acetic acid (R)-1-[(2S,3S)-1-benzyl-2-((S)-1-hydroxy-ethyl)-4-oxo-azetidin-3-yl]-ethyl ester

Base Information

Chemical Name:Acetic acid (R)-1-[(2S,3S)-1-benzyl-2-((S)-1-hydroxy-ethyl)-4-oxo-azetidin-3-yl]-ethyl ester
CAS No.:194367-32-3
Molecular Formula:C₁₆H₂₁NO₄
Molecular Weight:291.347
Hs Code.:

Synonyms:Acetic acid (R)-1-[(2S,3S)-1-benzyl-2-((S)-1-hydroxy-ethyl)-4-oxo-azetidin-3-yl]-ethyl ester

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Chemical Property of Acetic acid (R)-1-[(2S,3S)-1-benzyl-2-((S)-1-hydroxy-ethyl)-4-oxo-azetidin-3-yl]-ethyl ester

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Technology Process of Acetic acid (R)-1-[(2S,3S)-1-benzyl-2-((S)-1-hydroxy-ethyl)-4-oxo-azetidin-3-yl]-ethyl ester

There total 5 articles about Acetic acid (R)-1-[(2S,3S)-1-benzyl-2-((S)-1-hydroxy-ethyl)-4-oxo-azetidin-3-yl]-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: 77.0%

: 194367-31-2
Acetic acid (R)-1-{(2S,3S)-1-benzyl-2-[(S)-1-(tert-butyl-diphenyl-silanyloxy)-ethyl]-4-oxo-azetidin-3-yl}-ethyl ester

: 194367-32-3
Acetic acid (R)-1-[(2S,3S)-1-benzyl-2-((S)-1-hydroxy-ethyl)-4-oxo-azetidin-3-yl]-ethyl ester

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 4h; Ambient temperature;
DOI:10.1021/jo970435d

Reference yield:

: 161554-86-5
(2S,3S,4S)-2-((R)-1-Acetoxy-ethyl)-3-benzylamino-4-(tert-butyl-diphenyl-silanyloxy)-pentanoic acid tert-butyl ester

: 194367-32-3
Acetic acid (R)-1-[(2S,3S)-1-benzyl-2-((S)-1-hydroxy-ethyl)-4-oxo-azetidin-3-yl]-ethyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 1.) CF₃CO₂H, 2.) PPh₃, 2,2'-dipyridyl disulfide / 1) CH₂Cl₂, rt, overnight; 2) CH₃CN, reflux, 10 h

2: 77 percent / tetrabutylammonium fluoride / tetrahydrofuran / 4 h / Ambient temperature

With 2,2'-dipyridyldisulphide; tetrabutyl ammonium fluoride; triphenylphosphine; trifluoroacetic acid; In tetrahydrofuran;
DOI:10.1021/jo970435d

Reference yield:

: (E)-4-(tert-Butyl-diphenyl-silanyloxy)-pent-2-enoic acid methyl ester

: 194367-32-3
Acetic acid (R)-1-[(2S,3S)-1-benzyl-2-((S)-1-hydroxy-ethyl)-4-oxo-azetidin-3-yl]-ethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) n-BuLi / 1) n-hexane, THF, 0 deg C, 1 h; 2) n-hexane, THF, 0 deg C, overnight, rt, 2 h

2: 1.) n-BuLi / 1) THF, n-hexane, -78 deg C, 30 min; 2) THF, n-hexane, 1.5 h, -78 deg C

3: 1.) LDA, 3.) pyridine / 1) THF, -78 deg C, 20 min; 2) THF, -78 deg C, 1.5 h; 3) rt, 1 h

4: 1.) CF₃CO₂H, 2.) PPh₃, 2,2'-dipyridyl disulfide / 1) CH₂Cl₂, rt, overnight; 2) CH₃CN, reflux, 10 h

5: 77 percent / tetrabutylammonium fluoride / tetrahydrofuran / 4 h / Ambient temperature

With pyridine; n-butyllithium; 2,2'-dipyridyldisulphide; tetrabutyl ammonium fluoride; triphenylphosphine; trifluoroacetic acid; lithium diisopropyl amide; In tetrahydrofuran;
DOI:10.1021/jo970435d