(3S,4R)-1-(tert-Butyl-dimethyl-silanyl)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-{(1R,4R)-4-[(E)-3-(1,3-dimethyl-2-oxo-2λ⁵-[1,3,2]diazaphospholidin-2-yl)-allyl]-2-oxo-cyclohexyl}-azetidin-2-one

Base Information

• Chemical Name: (3S,4R)-1-(tert-Butyl-dimethyl-silanyl)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-{(1R,4R)-4-[(E)-3-(1,3-dimethyl-2-oxo-2λ⁵-[1,3,2]diazaphospholidin-2-yl)-allyl]-2-oxo-cyclohexyl}-azetidin-2-one
• CAS No.: 194535-46-1
• Molecular Formula: C₃₀H₅₈N₃O₄PSi₂
• Molecular Weight: 611.953

Synonyms:

Chemical Property of (3S,4R)-1-(tert-Butyl-dimethyl-silanyl)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-{(1R,4R)-4-[(E)-3-(1,3-dimethyl-2-oxo-2λ⁵-[1,3,2]diazaphospholidin-2-yl)-allyl]-2-oxo-cyclohexyl}-azetidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4R)-1-(tert-Butyl-dimethyl-silanyl)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-{(1R,4R)-4-[(E)-3-(1,3-dimethyl-2-oxo-2λ⁵-[1,3,2]diazaphospholidin-2-yl)-allyl]-2-oxo-cyclohexyl}-azetidin-2-one

There total 6 articles about (3S,4R)-1-(tert-Butyl-dimethyl-silanyl)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-{(1R,4R)-4-[(E)-3-(1,3-dimethyl-2-oxo-2λ⁵-[1,3,2]diazaphospholidin-2-yl)-allyl]-2-oxo-cyclohexyl}-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:

cyclohexenone (930-68-7) → (3S,4R)-1-(tert-Butyl-dimethyl-silanyl)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-{(1R,4R)-4-[(E)-3-(1,3-dimethyl-2-oxo-2λ5-[1,3,2]diazaphospholidin-2-yl)-allyl]-2-oxo-cyclohexyl}-azetidin-2-one (194535-46-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) LDA / 1.) THF, -78 deg C, 30 min, 2.) -78 deg C to room temperature, 2 h

2: 1.) NaH / 1.) THF, -20 deg C, 30 min, 2.) -20 deg C, 2 h

3: CH₂Cl₂ / 0.5 h / 0 °C

4: Pd(OAc)2, PPh₃, formic acid / ethyl acetate / 2 h / Heating

5: 1.) n-BuLi / 1.) THF, -78 deg C, 30 min, 2.) -78 deg C, 1 h

With palladium diacetate; n-butyllithium; formic acid; sodium hydride; triphenylphosphine; lithium diisopropyl amide; In dichloromethane; ethyl acetate;

DOI:10.1016/S0960-894X(97)00326-0

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)-1-(tert-Butyl-dimethyl-silanyl)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-{(1R,4R)-4-[(E)-3-(1,3-dimethyl-2-oxo-2λ5-[1,3,2]diazaphospholidin-2-yl)-allyl]-2-oxo-cyclohexyl}-azetidin-2-one (194535-46-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) NaH / 1.) THF, -20 deg C, 30 min, 2.) -20 deg C, 2 h

2: CH₂Cl₂ / 0.5 h / 0 °C

3: Pd(OAc)2, PPh₃, formic acid / ethyl acetate / 2 h / Heating

4: 1.) n-BuLi / 1.) THF, -78 deg C, 30 min, 2.) -78 deg C, 1 h

With palladium diacetate; n-butyllithium; formic acid; sodium hydride; triphenylphosphine; In dichloromethane; ethyl acetate;

DOI:10.1016/S0960-894X(97)00326-0

Reference yield:

allyl 2-oxocyclohex-3-ene-1-carboxylate (194535-42-7) → (3S,4R)-1-(tert-Butyl-dimethyl-silanyl)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-{(1R,4R)-4-[(E)-3-(1,3-dimethyl-2-oxo-2λ5-[1,3,2]diazaphospholidin-2-yl)-allyl]-2-oxo-cyclohexyl}-azetidin-2-one (194535-46-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) NaH / 1.) THF, -20 deg C, 30 min, 2.) -20 deg C, 2 h

2: CH₂Cl₂ / 0.5 h / 0 °C

3: Pd(OAc)2, PPh₃, formic acid / ethyl acetate / 2 h / Heating

4: 1.) n-BuLi / 1.) THF, -78 deg C, 30 min, 2.) -78 deg C, 1 h

With palladium diacetate; n-butyllithium; formic acid; sodium hydride; triphenylphosphine; In dichloromethane; ethyl acetate;

DOI:10.1016/S0960-894X(97)00326-0

upstream raw materials:

2-Allyl-1,3-dimethyl-[1,3,2]diazaphospholidine 2-oxide

(3S,4R)-1-(tert-Butyl-dimethyl-silanyl)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-((R)-2-oxo-cyclohex-3-enyl)-azetidin-2-one

cyclohexenone

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

Downstream raw materials:

((2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-{(1R,4R)-4-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-oxo-cyclohexyl}-4-oxo-azetidin-1-yl)-oxo-acetic acid benzyl ester

(1S,6S,8aS,8bR)-1-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-oxo-1,2,5,6,7,8,8a,8b-octahydro-azeto[2,1-a]isoindole-4-carboxylic acid benzyl ester

{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-[(1R,4R)-4-(2-methoxy-ethyl)-2-oxo-cyclohexyl]-4-oxo-azetidin-1-yl}-oxo-acetic acid benzyl ester

(1S,6S,8aS,8bR)-1-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-6-(2-methoxy-ethyl)-2-oxo-1,2,5,6,7,8,8a,8b-octahydro-azeto[2,1-a]isoindole-4-carboxylic acid benzyl ester

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