(3R,4S)-3-(1,3-butadien-2-yl)-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxy-1-(p-methoxyphenyl)-2-azetidinone

Base Information

Chemical Name:(3R,4S)-3-(1,3-butadien-2-yl)-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxy-1-(p-methoxyphenyl)-2-azetidinone
CAS No.:412272-08-3
Molecular Formula:C₁₉H₂₃NO₅
Molecular Weight:345.395
Hs Code.:

Synonyms:(3R,4S)-3-(1,3-butadien-2-yl)-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxy-1-(p-methoxyphenyl)-2-azetidinone

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Chemical Property of (3R,4S)-3-(1,3-butadien-2-yl)-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxy-1-(p-methoxyphenyl)-2-azetidinone

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Technology Process of (3R,4S)-3-(1,3-butadien-2-yl)-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxy-1-(p-methoxyphenyl)-2-azetidinone

There total 5 articles about (3R,4S)-3-(1,3-butadien-2-yl)-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxy-1-(p-methoxyphenyl)-2-azetidinone 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: 92.0%

: 2917-96-6
1,4-bis(methanesulfonyloxy)-2-butyne

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

: 412272-08-3
(3R,4S)-3-(1,3-butadien-2-yl)-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxy-1-(p-methoxyphenyl)-2-azetidinone

Guidance literature:: With indium; ammonium chloride; In tetrahydrofuran; for 4h;
DOI:10.1055/s-2003-39388

Reference yield: 54.0%

: 2219-66-1
1,4-dibromobut-2-yne

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

: 412272-08-3
(3R,4S)-3-(1,3-butadien-2-yl)-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxy-1-(p-methoxyphenyl)-2-azetidinone

Guidance literature:: With indium; water; In tetrahydrofuran; at 20 ℃; for 1h;
DOI:10.1055/s-2003-39388

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

: 412272-08-3
(3R,4S)-3-(1,3-butadien-2-yl)-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxy-1-(p-methoxyphenyl)-2-azetidinone

Guidance literature:: Multi-step reaction with 2 steps

1.1: dimethyl sulfoxide; oxalyl chloride / CH₂Cl₂ / 2 h / -78 °C

1.2: 77 percent / Et₃N / CH₂Cl₂ / -78 - 20 °C

2.1: 42 percent / indium; ammonium chloride; sodium iodide / tetrahydrofuran; H₂O / 0 - 20 °C

With indium; oxalyl dichloride; ammonium chloride; dimethyl sulfoxide; sodium iodide; In tetrahydrofuran; dichloromethane; water;
DOI:10.1021/jo016247b