(3R,4S)-3-(1,1-Dimethyl-allyl)-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-hydroxy-1-(4-methoxy-phenyl)-azetidin-2-one

Base Information

Chemical Name:(3R,4S)-3-(1,1-Dimethyl-allyl)-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-hydroxy-1-(4-methoxy-phenyl)-azetidin-2-one
CAS No.:358973-69-0
Molecular Formula:C₂₀H₂₇NO₅
Molecular Weight:361.438
Hs Code.:

Synonyms:(3R,4S)-3-(1,1-Dimethyl-allyl)-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-hydroxy-1-(4-methoxy-phenyl)-azetidin-2-one

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Chemical Property of (3R,4S)-3-(1,1-Dimethyl-allyl)-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-hydroxy-1-(4-methoxy-phenyl)-azetidin-2-one

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Technology Process of (3R,4S)-3-(1,1-Dimethyl-allyl)-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-hydroxy-1-(4-methoxy-phenyl)-azetidin-2-one

There total 4 articles about (3R,4S)-3-(1,1-Dimethyl-allyl)-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-hydroxy-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: 85.0%

: 153463-32-2
(S)-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(4-methoxyphenyl)azetidine-2,3-dione

: 870-63-3
prenyl bromide

: 358973-69-0
(3R,4S)-3-(1,1-Dimethyl-allyl)-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-hydroxy-1-(4-methoxy-phenyl)-azetidin-2-one

Guidance literature:: With ammonium chloride; zinc; In tetrahydrofuran; at 0 ℃; for 1.5h;
DOI:10.1021/jo015704l

Reference yield:

: 115828-87-0
(3R,4S)-cis-1-(p-anisyl)-3-hydroxy-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one

: 358973-69-0
(3R,4S)-3-(1,1-Dimethyl-allyl)-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-hydroxy-1-(4-methoxy-phenyl)-azetidin-2-one

Guidance literature:: Multi-step reaction with 2 steps

1: 77 percent / oxalyl chloride; dimethyl sulfoxide; triethylamine / CH₂Cl₂ / -78 - 20 °C

2: 85 percent / zinc powder; aq. NH₄Cl / tetrahydrofuran / 1.5 h / 0 °C

With oxalyl dichloride; ammonium chloride; dimethyl sulfoxide; triethylamine; zinc; In tetrahydrofuran; dichloromethane; 1: Swern oxidation;
DOI:10.1021/jo015704l

Reference yield:

: 141781-24-0
[1-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-meth-(E)-ylidene]-(4-methoxy-phenyl)-amine

: 358973-69-0
(3R,4S)-3-(1,1-Dimethyl-allyl)-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-hydroxy-1-(4-methoxy-phenyl)-azetidin-2-one

Guidance literature:: Multi-step reaction with 4 steps

1: 88 percent / Et₃N / CH₂Cl₂ / 16 h / 20 °C

2: 86 percent / sodium methoxide / methanol / 0.33 h / 0 °C

3: 77 percent / oxalyl chloride; dimethyl sulfoxide; triethylamine / CH₂Cl₂ / -78 - 20 °C

4: 85 percent / zinc powder; aq. NH₄Cl / tetrahydrofuran / 1.5 h / 0 °C

With oxalyl dichloride; sodium methylate; ammonium chloride; dimethyl sulfoxide; triethylamine; zinc; In tetrahydrofuran; methanol; dichloromethane; 1: Staudinger reaction / 3: Swern oxidation;
DOI:10.1021/jo015704l