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

Base Information

• Chemical Name: (3R,4S)-1-(4-methoxyphenyl)-3-triisopropylsiloxy-4-(2,2-difluorovinyl)azetidin-2-one
• CAS No.: 926306-99-2
• Molecular Formula: C₂₁H₃₁F₂NO₃Si
• Molecular Weight: 411.564

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

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

Chemical Property:

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

There total 9 articles about (3R,4S)-1-(4-methoxyphenyl)-3-triisopropylsiloxy-4-(2,2-difluorovinyl)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: 84.0%

dibromodifluoromethane (75-61-6) + (3R,4R)-1-(4-methoxyphenyl)-3-triisopropylsiloxy-4-formylazetidin-2-one (245657-85-6) → (3R,4S)-1-(4-methoxyphenyl)-3-triisopropylsiloxy-4-(2,2-difluorovinyl)azetidin-2-one (926306-99-2)

Guidance literature:

With zinc; Hexamethylphosphorous triamide; In tetrahydrofuran; at 0 ℃; Inert atmosphere; Reflux;

DOI:10.1016/j.jfluchem.2012.07.007

Reference yield:

sodium chlorodifluoroacetate (1895-39-2) + (3R,4R)-1-(4-methoxyphenyl)-3-triisopropylsiloxy-4-formylazetidin-2-one (245657-85-6) → (3R,4S)-1-(4-methoxyphenyl)-3-triisopropylsiloxy-4-(2,2-difluorovinyl)azetidin-2-one (926306-99-2)

Guidance literature:

With triphenylphosphine; In N,N-dimethyl-formamide; at 90 - 100 ℃; for 2h;

Reference yield:

(3R,4S)-1-(4-methoxyphenyl)-3-triisopropylsiloxy-4-(2-methylprop-1-enyl)azetidin-2-one (178250-07-2) → (3R,4S)-1-(4-methoxyphenyl)-3-triisopropylsiloxy-4-(2,2-difluorovinyl)azetidin-2-one (926306-99-2)

Guidance literature:

Multi-step reaction with 2 steps

1: ozone / dichloromethane; methanol / -78 °C

2: zinc; Hexamethylphosphorous triamide / tetrahydrofuran / 0 °C / Inert atmosphere; Reflux

With ozone; zinc; Hexamethylphosphorous triamide; In tetrahydrofuran; methanol; dichloromethane; 2: |Wittig Olefination;

DOI:10.1016/j.jfluchem.2012.07.007

upstream raw materials:

dibromodifluoromethane

(3R,4R)-1-(4-methoxyphenyl)-3-triisopropylsiloxy-4-formylazetidin-2-one

(3R,4S)-1-(4-methoxyphenyl)-3-acetoxy-4-(2-methyl-1-propenyl)azetidin-2-one

(3R,4S)-3-Hydroxy-1-(4-methoxy-phenyl)-4-(2-methyl-propenyl)-azetidin-2-one

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