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

Base Information

Chemical Name:(5S,6S)-6-((R)-1-Allyloxycarbonyloxy-ethyl)-4,4-difluoro-7-oxo-3-phenyl-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester
CAS No.:111969-61-0
Molecular Formula:C₂₂H₂₁F₂NO₆
Molecular Weight:433.409
Hs Code.:

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

There total 13 articles about (5S,6S)-6-((R)-1-Allyloxycarbonyloxy-ethyl)-4,4-difluoro-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: 41.0%

: 111969-62-1,112020-50-5
[(2S,3S)-3-((R)-1-Allyloxycarbonyloxy-ethyl)-2-(1,1-difluoro-2-oxo-2-phenyl-ethyl)-4-oxo-azetidin-1-yl]-bromo-acetic acid allyl ester

: 111969-61-0
(5S,6S)-6-((R)-1-Allyloxycarbonyloxy-ethyl)-4,4-difluoro-7-oxo-3-phenyl-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester

Guidance literature:: With 2,6-dimethylpyridine; triphenylphosphine; In tetrahydrofuran; at 40 ℃; for 18h;

Reference yield:

: 111969-60-9,112020-49-2
[(2S,3S)-3-((R)-1-Allyloxycarbonyloxy-ethyl)-2-(1,1-difluoro-2-oxo-2-phenyl-ethyl)-4-oxo-azetidin-1-yl]-chloro-acetic acid allyl ester

: 111969-61-0
(5S,6S)-6-((R)-1-Allyloxycarbonyloxy-ethyl)-4,4-difluoro-7-oxo-3-phenyl-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester

Guidance literature:: With 2,6-dimethylpyridine; triphenylphosphine; In tetrahydrofuran; at 40 ℃; for 18h;

Reference yield:

: 384-67-8
2-chloro-2,2-difluoroacetophenone

: 111969-61-0
(5S,6S)-6-((R)-1-Allyloxycarbonyloxy-ethyl)-4,4-difluoro-7-oxo-3-phenyl-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: Zn / acetonitrile / 60 °C

2: 20 percent / TiCl₄ / CH₂Cl₂ / 24 h / Heating

3: 1.) LDA, HMPA / 1.) THF, -78 deg C, 2.) THF, from -78 degC to 0 deg C

4: 73 percent / 10percent H₂SO₄ / methanol / 1 h / Ambient temperature

5: 83 percent / DMAP / CH₂Cl₂ / 2 h / Ambient temperature

6: 97 percent / 2-mercaptopyridine, Et₃N / CH₂Cl₂

7: 66 percent / Et₃N, 3A molecular sieve / toluene / 18 h / Ambient temperature

8: 62 percent / SOCl₂, 2,6-lutidine / tetrahydrofuran / 0.5 h / -10 °C

9: PPh₃, 2,6-lutidine / tetrahydrofuran / 18 h / 40 °C

With 2,6-dimethylpyridine; 2-Sulfanylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; thionyl chloride; 3 A molecular sieve; sulfuric acid; titanium tetrachloride; triethylamine; triphenylphosphine; zinc; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; toluene; acetonitrile;