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CAS No.: | 67977-91-7 |
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Name: | (2R,6R,7R)-7-(Benzoylamino)-3-methylene-8-oxo-5-oxa-1-azabicyclo[4.2.0]octane-2-carboxylic acid diphenylmethyl ester |
Article Data: | 4 |
Molecular Structure: | |
Formula: | C28H24N2O5 |
Molecular Weight: | 468.509 |
Synonyms: | (2R,6R,7R)-7-(benzoylamino)-3-methylene-8-oxo-5-Oxa-1-azabicyclo[4.2.0]octane-2-carboxylic acid diphenylmethyl ester; |
EINECS: | 1308068-626-2 |
Density: | 1.34 |
Boiling Point: | 706.8±60.0 °C(Predicted) |
PSA: | 88.43000 |
LogP: | 3.75380 |
(R)-3-Hydroxymethyl-2-((1R,5S)-7-oxo-3-phenyl-4-oxa-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-but-3-enoic acid benzhydryl ester
(2R,6R,7R)-7-Benzoylamino-3-methylene-8-oxo-5-oxa-1-aza-bicyclo[4.2.0]octane-2-carboxylic acid benzhydryl ester
Conditions | Yield |
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boron trifluoride diethyl etherate In ethyl acetate at 25℃; | 90% |
epi-Secopenicillin
(2R,6R,7R)-7-Benzoylamino-3-methylene-8-oxo-5-oxa-1-aza-bicyclo[4.2.0]octane-2-carboxylic acid benzhydryl ester
Conditions | Yield |
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Multi-step reaction with 5 steps 1: chlorine / ethyl acetate / 20 - 30 °C 2: NaHCO3 / H2O / 20 - 30 °C 3: 88 percent / NaNO3, methyl p-toluenesulfonate / dimethylsulfoxide / 55 °C / 50 Torr 4: 85 percent / Zn, AcOH / CH2Cl2 / 0 °C 5: 90 percent / BF3*Et2O / ethyl acetate / 25 °C View Scheme | |
Multi-step reaction with 6 steps 1: chlorine / ethyl acetate / 20 - 30 °C 2: NaHCO3 / H2O / 20 - 30 °C 3: PhSNa / acetone; methanol / 35 °C 4: m-chloroperbenzoic acid / CH2Cl2 / -10 °C 5: methanol; benzene / Heating 6: 90 percent / BF3*Et2O / ethyl acetate / 25 °C View Scheme |
(R)-3-chloromethyl-2-((1R)-7-oxo-3-phenyl-(1rH,5cH)-4-oxa-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-but-3-enoic acid benzhydryl ester
(2R,6R,7R)-7-Benzoylamino-3-methylene-8-oxo-5-oxa-1-aza-bicyclo[4.2.0]octane-2-carboxylic acid benzhydryl ester
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 88 percent / NaNO3, methyl p-toluenesulfonate / dimethylsulfoxide / 55 °C / 50 Torr 2: 85 percent / Zn, AcOH / CH2Cl2 / 0 °C 3: 90 percent / BF3*Et2O / ethyl acetate / 25 °C View Scheme | |
Multi-step reaction with 4 steps 1: PhSNa / acetone; methanol / 35 °C 2: m-chloroperbenzoic acid / CH2Cl2 / -10 °C 3: methanol; benzene / Heating 4: 90 percent / BF3*Et2O / ethyl acetate / 25 °C View Scheme |
(R)-2-((1R,5S)-7-Oxo-3-phenyl-4-oxa-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-3-phenylsulfanylmethyl-but-3-enoic acid benzhydryl ester
(2R,6R,7R)-7-Benzoylamino-3-methylene-8-oxo-5-oxa-1-aza-bicyclo[4.2.0]octane-2-carboxylic acid benzhydryl ester
Conditions | Yield |
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Multi-step reaction with 3 steps 1: m-chloroperbenzoic acid / CH2Cl2 / -10 °C 2: methanol; benzene / Heating 3: 90 percent / BF3*Et2O / ethyl acetate / 25 °C View Scheme |
(R)-3-Nitrooxymethyl-2-((1R,5S)-7-oxo-3-phenyl-4-oxa-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-but-3-enoic acid benzhydryl ester
(2R,6R,7R)-7-Benzoylamino-3-methylene-8-oxo-5-oxa-1-aza-bicyclo[4.2.0]octane-2-carboxylic acid benzhydryl ester
Conditions | Yield |
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Multi-step reaction with 2 steps 1: 85 percent / Zn, AcOH / CH2Cl2 / 0 °C 2: 90 percent / BF3*Et2O / ethyl acetate / 25 °C View Scheme |
(2R,6R,7R)-7-Benzoylamino-3-methylene-8-oxo-5-oxa-1-aza-bicyclo[4.2.0]octane-2-carboxylic acid benzhydryl ester
Conditions | Yield |
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Multi-step reaction with 2 steps 1: methanol; benzene / Heating 2: 90 percent / BF3*Et2O / ethyl acetate / 25 °C View Scheme |
Diphenylmethyl-2-(3R,4R-3-benzamido-4-chlor-2-oxo-azetidin-1-yl)-3-chlormethyl-3-butenoat
(2R,6R,7R)-7-Benzoylamino-3-methylene-8-oxo-5-oxa-1-aza-bicyclo[4.2.0]octane-2-carboxylic acid benzhydryl ester
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: NaHCO3 / H2O / 20 - 30 °C 2: 88 percent / NaNO3, methyl p-toluenesulfonate / dimethylsulfoxide / 55 °C / 50 Torr 3: 85 percent / Zn, AcOH / CH2Cl2 / 0 °C 4: 90 percent / BF3*Et2O / ethyl acetate / 25 °C View Scheme | |
Multi-step reaction with 5 steps 1: NaHCO3 / H2O / 20 - 30 °C 2: PhSNa / acetone; methanol / 35 °C 3: m-chloroperbenzoic acid / CH2Cl2 / -10 °C 4: methanol; benzene / Heating 5: 90 percent / BF3*Et2O / ethyl acetate / 25 °C View Scheme |
6-epipenicillin sulfoxide
(2R,6R,7R)-7-Benzoylamino-3-methylene-8-oxo-5-oxa-1-aza-bicyclo[4.2.0]octane-2-carboxylic acid benzhydryl ester
Conditions | Yield |
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Multi-step reaction with 6 steps 1: 80 percent / PPh3 / toluene; CH2Cl2 / Heating 2: chlorine / ethyl acetate / 20 - 30 °C 3: NaHCO3 / H2O / 20 - 30 °C 4: 88 percent / NaNO3, methyl p-toluenesulfonate / dimethylsulfoxide / 55 °C / 50 Torr 5: 85 percent / Zn, AcOH / CH2Cl2 / 0 °C 6: 90 percent / BF3*Et2O / ethyl acetate / 25 °C View Scheme | |
Multi-step reaction with 7 steps 1: 80 percent / PPh3 / toluene; CH2Cl2 / Heating 2: chlorine / ethyl acetate / 20 - 30 °C 3: NaHCO3 / H2O / 20 - 30 °C 4: PhSNa / acetone; methanol / 35 °C 5: m-chloroperbenzoic acid / CH2Cl2 / -10 °C 6: methanol; benzene / Heating 7: 90 percent / BF3*Et2O / ethyl acetate / 25 °C View Scheme |
(2R,6R,7R)-7-Benzoylamino-3-methylene-8-oxo-5-oxa-1-aza-bicyclo[4.2.0]octane-2-carboxylic acid benzhydryl ester
(2S,6R,7R)-7-Benzoylamino-3-chloro-3-hydroxymethyl-8-oxo-5-oxa-1-aza-bicyclo[4.2.0]octane-2-carboxylic acid benzhydryl ester
Conditions | Yield |
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With perchloric acid; trichloroisocyanuric acid In acetone at 25℃; | 100% |
(2R,6R,7R)-7-Benzoylamino-3-methylene-8-oxo-5-oxa-1-aza-bicyclo[4.2.0]octane-2-carboxylic acid benzhydryl ester
(6R)-7c-benzoylamino-3-methyl-8-oxo-(6rH)-5-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester
Conditions | Yield |
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With triethylamine In dichloromethane at 25℃; for 1h; |