(3R,4S)-1-(4-methoxyphenyl)-3-triisopropylsiloxy-4-(1-acetoxyprop-2-enyl)azetidin-2-one

Base Information

Chemical Name:(3R,4S)-1-(4-methoxyphenyl)-3-triisopropylsiloxy-4-(1-acetoxyprop-2-enyl)azetidin-2-one
CAS No.:286932-20-5
Molecular Formula:C₂₄H₃₇NO₅Si
Molecular Weight:447.647
Hs Code.:

Synonyms:(3R,4S)-1-(4-methoxyphenyl)-3-triisopropylsiloxy-4-(1-acetoxyprop-2-enyl)azetidin-2-one

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Chemical Property of (3R,4S)-1-(4-methoxyphenyl)-3-triisopropylsiloxy-4-(1-acetoxyprop-2-enyl)azetidin-2-one

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Technology Process of (3R,4S)-1-(4-methoxyphenyl)-3-triisopropylsiloxy-4-(1-acetoxyprop-2-enyl)azetidin-2-one

There total 2 articles about (3R,4S)-1-(4-methoxyphenyl)-3-triisopropylsiloxy-4-(1-acetoxyprop-2-enyl)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: 98.0%

: 1826-67-1
vinyl magnesium bromide

: 108-24-7
acetic anhydride

: 245657-85-6
(3R,4R)-1-(4-methoxyphenyl)-3-triisopropylsiloxy-4-formylazetidin-2-one

: 286932-20-5
(3R,4S)-1-(4-methoxyphenyl)-3-triisopropylsiloxy-4-(1-acetoxyprop-2-enyl)azetidin-2-one

Guidance literature:: vinyl magnesium bromide; (3R,4R)-1-(4-methoxyphenyl)-3-triisopropylsiloxy-4-formylazetidin-2-one; In tetrahydrofuran; at -78 ℃; for 0.5h;

acetic anhydride; at -78 - 20 ℃; Further stages.;
DOI:10.1021/ja000293w

Reference yield:

: 178250-07-2
(3R,4S)-1-(4-methoxyphenyl)-3-triisopropylsiloxy-4-(2-methylprop-1-enyl)azetidin-2-one

: 286932-20-5
(3R,4S)-1-(4-methoxyphenyl)-3-triisopropylsiloxy-4-(1-acetoxyprop-2-enyl)azetidin-2-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: O₃ / methanol; CH₂Cl₂ / 0.03 h / -78 °C

1.2: 100 percent / dimethyl sulfide / methanol; CH₂Cl₂ / 3 h / -78 - 20 °C

2.1: tetrahydrofuran / 0.5 h / -78 °C

2.2: 98 percent / -78 - 20 °C

With ozone; In tetrahydrofuran; methanol; dichloromethane; 1.1: ozonolysis / 1.2: Reduction / 2.1: Addition / 2.2: Acetylation;
DOI:10.1021/ja000293w

Reference yield: 65.0%

: 286932-20-5
(3R,4S)-1-(4-methoxyphenyl)-3-triisopropylsiloxy-4-(1-acetoxyprop-2-enyl)azetidin-2-one

: 286933-03-7
(3R,4S)-1-(4-methoxyphenyl)-3-triisopropylsiloxy-4-(prop-2-enyl)azetidin-2-one

Guidance literature:: With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; tributylphosphine; ammonium formate; In 1,4-dioxane; for 18h; Heating;
DOI:10.1021/ja000293w