(4R,5S,6S)-6-((R)-1-Allyloxycarbonyloxy-ethyl)-4-fluoro-4-methyl-7-oxo-3-phenyl-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester

Base Information

Chemical Name:(4R,5S,6S)-6-((R)-1-Allyloxycarbonyloxy-ethyl)-4-fluoro-4-methyl-7-oxo-3-phenyl-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester
CAS No.:168780-16-3
Molecular Formula:C₂₃H₂₄FNO₆
Molecular Weight:429.445
Hs Code.:

Synonyms:(4R,5S,6S)-6-((R)-1-Allyloxycarbonyloxy-ethyl)-4-fluoro-4-methyl-7-oxo-3-phenyl-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester

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Chemical Property of (4R,5S,6S)-6-((R)-1-Allyloxycarbonyloxy-ethyl)-4-fluoro-4-methyl-7-oxo-3-phenyl-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester

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Technology Process of (4R,5S,6S)-6-((R)-1-Allyloxycarbonyloxy-ethyl)-4-fluoro-4-methyl-7-oxo-3-phenyl-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester

There total 12 articles about (4R,5S,6S)-6-((R)-1-Allyloxycarbonyloxy-ethyl)-4-fluoro-4-methyl-7-oxo-3-phenyl-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic 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: 53.0%

: 168780-15-2
[(2S,3S)-3-((R)-1-Allyloxycarbonyloxy-ethyl)-2-((S)-1-fluoro-1-methyl-2-oxo-2-phenyl-ethyl)-4-oxo-azetidin-1-yl]-oxo-acetic acid allyl ester

: 168780-16-3
(4R,5S,6S)-6-((R)-1-Allyloxycarbonyloxy-ethyl)-4-fluoro-4-methyl-7-oxo-3-phenyl-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester

Guidance literature:: With triethyl phosphite; In xylene; at 110 ℃;

Reference yield:

: 74503-07-4
allyl oxalyl chloride

: 168780-16-3
(4R,5S,6S)-6-((R)-1-Allyloxycarbonyloxy-ethyl)-4-fluoro-4-methyl-7-oxo-3-phenyl-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: pyridine / CH₂Cl₂

2: 53 percent / P(OEt)3 / xylene / 110 °C

With pyridine; triethyl phosphite; In dichloromethane; xylene;

Reference yield:

: 87037-97-6
methyl (2R)-2-[(2S,3S)-3-{(1R)-1-(t-butyldimethylsilyloxy)ethyl}-4-oxoazetidin-2-yl]propionate

: 168780-16-3
(4R,5S,6S)-6-((R)-1-Allyloxycarbonyloxy-ethyl)-4-fluoro-4-methyl-7-oxo-3-phenyl-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester

Guidance literature:: Multi-step reaction with 10 steps

1: 1.) LDA, 2.) N-fluoro-N-(exo-2-norbornyl)-p-toluenesulfonamide / 1.) HMPA, THF, -78 deg C, 2.) HMPA, THF, from -78 deg C to RT

2: 1N aq. LiOH

3: PPh₃ / CH₂Cl₂

4: Et₃N / CH₂Cl₂

5: tetrahydrofuran

6: BF₃*Et₂O / acetonitrile

7: DMAP / CH₂Cl₂

8: TBAF, HOAc / tetrahydrofuran

9: pyridine / CH₂Cl₂

10: 53 percent / P(OEt)3 / xylene / 110 °C

With pyridine; dmap; lithium hydroxide; N-fluoro-N-(exo-2-norbornyl)-p-toluenesulfonamide; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; acetic acid; triethylamine; triphenylphosphine; lithium diisopropyl amide; triethyl phosphite; In tetrahydrofuran; dichloromethane; acetonitrile; xylene;