1-{(2S,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-2-oxo-cyclohex-3-enecarboxylic acid allyl ester

Base Information

• Chemical Name: 1-{(2S,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-2-oxo-cyclohex-3-enecarboxylic acid allyl ester
• CAS No.: 194535-43-8
• Molecular Formula: C₂₁H₃₃NO₅Si
• Molecular Weight: 407.582
• Mol file: 194535-43-8.mol

Synonyms:

Chemical Property of 1-{(2S,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-2-oxo-cyclohex-3-enecarboxylic acid allyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-{(2S,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-2-oxo-cyclohex-3-enecarboxylic acid allyl ester

There total 2 articles about 1-{(2S,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-2-oxo-cyclohex-3-enecarboxylic 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:

cyclohexenone (930-68-7) → 1-{(2S,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-2-oxo-cyclohex-3-enecarboxylic acid allyl ester (194535-43-8)

Guidance literature:

Multi-step reaction with 2 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

With sodium hydride; lithium diisopropyl amide;

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) + allyl 2-oxocyclohex-3-ene-1-carboxylate (194535-42-7) → 1-{(2S,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-2-oxo-cyclohex-3-enecarboxylic acid allyl ester (194535-43-8)

Guidance literature:

With sodium hydride; Multistep reaction; 1.) THF, -20 deg C, 30 min, 2.) -20 deg C, 2 h;

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

Reference yield:

1-{(2S,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-2-oxo-cyclohex-3-enecarboxylic acid allyl ester (194535-43-8) → (1S,6S,8aS,8bR)-1-((R)-1-Hydroxy-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 (194535-57-4)

Guidance literature:

Multi-step reaction with 10 steps

1: CH₂Cl₂ / 0.5 h / 0 °C

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

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

4: 1.) O₃, 2.) Me₂S / 1.) CH₂Cl₂, -78 deg C, 2.) -78 deg C to room temperature, 1 h

5: 95 percent / 9-BBN / tetrahydrofuran / 12 h

6: 94 percent / Ag₂O / 5 h / Heating

7: 74 percent / TBAF, AcOH / tetrahydrofuran / 0.5 h / Ambient temperature

8: 87 percent / pyridine / CH₂Cl₂ / 2 h / 0 °C

9: 71 percent / P(OEt)3 / o-xylene / 7 h / 140 °C

10: 75 percent / TBAF, AcOH / tetrahydrofuran / 96 h

With pyridine; palladium diacetate; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; formic acid; dimethylsulfide; tetrabutyl ammonium fluoride; ozone; acetic acid; triphenylphosphine; silver(l) oxide; triethyl phosphite; In tetrahydrofuran; dichloromethane; o-xylene; ethyl acetate;

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

upstream raw materials:

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

allyl 2-oxocyclohex-3-ene-1-carboxylate

cyclohexenone

Downstream raw materials:

1-{(2S,3S)-1-(tert-Butyl-dimethyl-silanyl)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-2-oxo-cyclohex-3-enecarboxylic acid allyl ester

(3S,4R)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-[(1R,4R)-4-(2-methoxy-ethyl)-2-oxo-cyclohexyl]-azetidin-2-one

(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

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