(1R,5S)-3-phenyl-6-(1-diphenylmethoxycarbonyl-2-methylprop-1-enyl)-7-oxo-4-oxa-2,6-diazabicyclo[3.2.0]hept-2-ene

Base Information

• Chemical Name: (1R,5S)-3-phenyl-6-(1-diphenylmethoxycarbonyl-2-methylprop-1-enyl)-7-oxo-4-oxa-2,6-diazabicyclo[3.2.0]hept-2-ene
• CAS No.: 68057-04-5
• Molecular Formula: C₂₈H₂₄N₂O₄
• Molecular Weight: 452.51
• Mol file: 68057-04-5.mol

Synonyms:(1R,5S)-3-phenyl-6-(1-diphenylmethoxycarbonyl-2-methylprop-1-enyl)-7-oxo-4-oxa-2,6-diazabicyclo[3.2.0]hept-2-ene

Chemical Property of (1R,5S)-3-phenyl-6-(1-diphenylmethoxycarbonyl-2-methylprop-1-enyl)-7-oxo-4-oxa-2,6-diazabicyclo[3.2.0]hept-2-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,5S)-3-phenyl-6-(1-diphenylmethoxycarbonyl-2-methylprop-1-enyl)-7-oxo-4-oxa-2,6-diazabicyclo[3.2.0]hept-2-ene

There total 2 articles about (1R,5S)-3-phenyl-6-(1-diphenylmethoxycarbonyl-2-methylprop-1-enyl)-7-oxo-4-oxa-2,6-diazabicyclo[3.2.0]hept-2-ene 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: 97.0%

epi-Secopenicillin (67977-61-1,68107-98-2) → (1R,5S)-3-phenyl-6-(1-diphenylmethoxycarbonyl-2-methylprop-1-enyl)-7-oxo-4-oxa-2,6-diazabicyclo[3.2.0]hept-2-ene (68057-04-5)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at -45 ℃; for 2h; Solvent; Reagent/catalyst; Temperature;

Reference yield: 93.0%

(2S,5R,6R)-6-Benzoylamino-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester (64324-01-2) → 3-Methyl-2-((1S,5R)-7-oxo-3-phenyl-4-oxa-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-but-2-enoic acid benzhydryl ester (68057-04-5,94480-95-2)

Guidance literature:

With magnesium chloride; In methanol; tert-butyl alcohol; at -40 ℃; electrolysis, Pt electrodes, 10 mA/cm²;

DOI:10.1002/bscb.19820911202

Reference yield: 53.0%

(S)-Ethyl lactate (687-47-8) + (1R,5S)-3-phenyl-6-(1-diphenylmethoxycarbonyl-2-methylprop-1-enyl)-7-oxo-4-oxa-2,6-diazabicyclo[3.2.0]hept-2-ene (68057-04-5) → (3R,4R)-4-{(1S)-1-ethoxycarbonylethoxy}-3-benzamido-1-(1-diphenylmethoxycarbonyl-2-methylprop-1-enyl)-azetidin-2-one (90211-50-0)

Guidance literature:

With trifluorormethanesulfonic acid; for 1.5h; Ambient temperature;

DOI:10.3987/COM-90-5344

upstream raw materials:

epi-Secopenicillin

(2S,5R,6R)-6-Benzoylamino-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester

Downstream raw materials:

(3R,4R)-4-{(1S)-1-ethoxycarbonylethoxy}-3-benzamido-1-(1-diphenylmethoxycarbonyl-2-methylprop-1-enyl)-azetidin-2-one

(3R,4R)-4-{(1R)-1-ethoxycarbonylethoxy}-3-benzamido-1-(1-diphenylmethoxycarbonyl-2-methylprop-1-enyl)azetidin-2-one

diphenylmethyl 2-[(1R,5S)-3-phenyl-7-oxo-4-oxa-2,6-diazabicyclo[3.2.0]hept-2-en-6-yl]-2-oxo acetate

(1R,5S)-3-phenyl-7-oxo-4-oxa-2,6-diazabicyclo[3.2.0]hept-2-ene