(3S,4S)-4-((4S,5S)-4,5-Bis-methoxymethyl-2-methyl-[1,3]dioxolan-2-yl)-3-((R)-1-hydroxy-ethyl)-1-(4-methoxy-phenyl)-azetidin-2-one

Base Information

Chemical Name:(3S,4S)-4-((4S,5S)-4,5-Bis-methoxymethyl-2-methyl-[1,3]dioxolan-2-yl)-3-((R)-1-hydroxy-ethyl)-1-(4-methoxy-phenyl)-azetidin-2-one
CAS No.:172944-57-9
Molecular Formula:C₂₀H₂₉NO₇
Molecular Weight:395.453
Hs Code.:

Synonyms:(3S,4S)-4-((4S,5S)-4,5-Bis-methoxymethyl-2-methyl-[1,3]dioxolan-2-yl)-3-((R)-1-hydroxy-ethyl)-1-(4-methoxy-phenyl)-azetidin-2-one

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Chemical Property of (3S,4S)-4-((4S,5S)-4,5-Bis-methoxymethyl-2-methyl-[1,3]dioxolan-2-yl)-3-((R)-1-hydroxy-ethyl)-1-(4-methoxy-phenyl)-azetidin-2-one

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Technology Process of (3S,4S)-4-((4S,5S)-4,5-Bis-methoxymethyl-2-methyl-[1,3]dioxolan-2-yl)-3-((R)-1-hydroxy-ethyl)-1-(4-methoxy-phenyl)-azetidin-2-one

There total 1 articles about (3S,4S)-4-((4S,5S)-4,5-Bis-methoxymethyl-2-methyl-[1,3]dioxolan-2-yl)-3-((R)-1-hydroxy-ethyl)-1-(4-methoxy-phenyl)-azetidin-2-one 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:

: 2466-76-4
N-Acetylimidazole

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

: (3S,4S)-4-((4S,5S)-4,5-Bis-methoxymethyl-2-methyl-[1,3]dioxolan-2-yl)-3-((S)-1-hydroxy-ethyl)-1-(4-methoxy-phenyl)-azetidin-2-one

: 172944-57-9
(3S,4S)-4-((4S,5S)-4,5-Bis-methoxymethyl-2-methyl-[1,3]dioxolan-2-yl)-3-((R)-1-hydroxy-ethyl)-1-(4-methoxy-phenyl)-azetidin-2-one

Guidance literature:: With diisobutylaluminium hydride; Yield given. Multistep reaction;
DOI:10.1246/cl.1995.1013

Reference yield: 97.0%

: 172944-57-9
(3S,4S)-4-((4S,5S)-4,5-Bis-methoxymethyl-2-methyl-[1,3]dioxolan-2-yl)-3-((R)-1-hydroxy-ethyl)-1-(4-methoxy-phenyl)-azetidin-2-one

: 104485-43-0
(3S,4S)-1-(4-methoxyphenyl)-3-[((R)-1-hydroxyethyl)]-4-acetyl-2-azetidinone

Guidance literature:: With trifluorormethanesulfonic acid; In butanone;
DOI:10.1246/cl.1995.1013

Reference yield:

: 172944-57-9
(3S,4S)-4-((4S,5S)-4,5-Bis-methoxymethyl-2-methyl-[1,3]dioxolan-2-yl)-3-((R)-1-hydroxy-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 5 steps

1: 97 percent / CF₃SO₃H / butan-2-one

2: imidazole / dimethylformamide / Ambient temperature

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

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

5: 98 percent / HCOOH, Pd(OAc)2, PPh₃ / dioxane / 22 h / 90 °C

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