[(3S,4R)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-oxo-4-((S)-2-oxo-cyclopentyl)-azetidin-1-yl]-(triphenyl-λ⁵-phosphanylidene)-acetic acid allyl ester

Base Information

• Chemical Name: [(3S,4R)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-oxo-4-((S)-2-oxo-cyclopentyl)-azetidin-1-yl]-(triphenyl-λ⁵-phosphanylidene)-acetic acid allyl ester
• CAS No.: 175880-80-5
• Molecular Formula: C₃₉H₄₈NO₅PSi
• Molecular Weight: 669.873

Synonyms:

Chemical Property of [(3S,4R)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-oxo-4-((S)-2-oxo-cyclopentyl)-azetidin-1-yl]-(triphenyl-λ⁵-phosphanylidene)-acetic acid allyl ester

Chemical Property:

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Safty Information:

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Useful:

Technology Process of [(3S,4R)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-oxo-4-((S)-2-oxo-cyclopentyl)-azetidin-1-yl]-(triphenyl-λ⁵-phosphanylidene)-acetic acid allyl ester

There total 4 articles about [(3S,4R)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-oxo-4-((S)-2-oxo-cyclopentyl)-azetidin-1-yl]-(triphenyl-λ⁵-phosphanylidene)-acetic acid allyl ester 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:

(3R,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one (76899-07-5,78963-47-0,78963-48-1,78963-60-7,80951-41-3,81275-02-7,85647-75-2,85954-95-6,92217-74-8,104527-11-9,76855-69-1) → [(3S,4R)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-oxo-4-((S)-2-oxo-cyclopentyl)-azetidin-1-yl]-(triphenyl-λ5-phosphanylidene)-acetic acid allyl ester (175880-80-5)

Guidance literature:

Multi-step reaction with 4 steps

1: Et₃N / tetrahydrofuran / 0 °C

2: (CH₃)3SiOTf / CH₂Cl₂ / 0 °C

3: KF / methanol

4: 2.) SOCl₂, lutidine / 1.) toluene, reflux, 2.) THF, -20 deg C

With potassium fluoride; thionyl chloride; trimethylsilyl trifluoromethanesulfonate; lutidine; triethylamine; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1016/0960-894X(96)00061-3

Reference yield:

(3R,4R)-4-acetoxy-3-[(R)-1-(t-butyldimethylsilyloxy)ethyl]-1-trimethylsilyl-2-azetidinone (86978-81-6) → [(3S,4R)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-oxo-4-((S)-2-oxo-cyclopentyl)-azetidin-1-yl]-(triphenyl-λ5-phosphanylidene)-acetic acid allyl ester (175880-80-5)

Guidance literature:

Multi-step reaction with 3 steps

1: (CH₃)3SiOTf / CH₂Cl₂ / 0 °C

2: KF / methanol

3: 2.) SOCl₂, lutidine / 1.) toluene, reflux, 2.) THF, -20 deg C

With potassium fluoride; thionyl chloride; trimethylsilyl trifluoromethanesulfonate; lutidine; In methanol; dichloromethane;

DOI:10.1016/0960-894X(96)00061-3

Reference yield:

(3S,4R)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-(2-oxo-cyclopentyl)-1-trimethylsilanyl-azetidin-2-one → [(3S,4R)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-oxo-4-((S)-2-oxo-cyclopentyl)-azetidin-1-yl]-(triphenyl-λ5-phosphanylidene)-acetic acid allyl ester (175880-80-5)

Guidance literature:

Multi-step reaction with 2 steps

1: KF / methanol

2: 2.) SOCl₂, lutidine / 1.) toluene, reflux, 2.) THF, -20 deg C

With potassium fluoride; thionyl chloride; lutidine; In methanol;

DOI:10.1016/0960-894X(96)00061-3

upstream raw materials:

allyl 2-oxoacetate

triphenylphosphine

(3R,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one

(3R,4R)-4-acetoxy-3-[(R)-1-(t-butyldimethylsilyloxy)ethyl]-1-trimethylsilyl-2-azetidinone

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