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67977-91-7

Basic Information
CAS No.: 67977-91-7
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:
Molecular Structure of 67977-91-7 ((2R,6R,7R)-7-(Benzoylamino)-3-methylene-8-oxo-5-oxa-1-azabicyclo[4.2.0]octane-2-carboxylic acid diphenylmethyl ester)
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
Synthetic route
67977-88-2

(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

67977-91-7

(2R,6R,7R)-7-Benzoylamino-3-methylene-8-oxo-5-oxa-1-aza-bicyclo[4.2.0]octane-2-carboxylic acid benzhydryl ester

Conditions
ConditionsYield
boron trifluoride diethyl etherate In ethyl acetate at 25℃;90%
67977-61-1

epi-Secopenicillin

67977-91-7

(2R,6R,7R)-7-Benzoylamino-3-methylene-8-oxo-5-oxa-1-aza-bicyclo[4.2.0]octane-2-carboxylic acid benzhydryl ester

Conditions
ConditionsYield
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
67977-79-1

(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

67977-91-7

(2R,6R,7R)-7-Benzoylamino-3-methylene-8-oxo-5-oxa-1-aza-bicyclo[4.2.0]octane-2-carboxylic acid benzhydryl ester

Conditions
ConditionsYield
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
67977-85-9

(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

67977-91-7

(2R,6R,7R)-7-Benzoylamino-3-methylene-8-oxo-5-oxa-1-aza-bicyclo[4.2.0]octane-2-carboxylic acid benzhydryl ester

Conditions
ConditionsYield
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
67977-90-6

(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

67977-91-7

(2R,6R,7R)-7-Benzoylamino-3-methylene-8-oxo-5-oxa-1-aza-bicyclo[4.2.0]octane-2-carboxylic acid benzhydryl ester

Conditions
ConditionsYield
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

C34H28N2O5S

67977-91-7

(2R,6R,7R)-7-Benzoylamino-3-methylene-8-oxo-5-oxa-1-aza-bicyclo[4.2.0]octane-2-carboxylic acid benzhydryl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: methanol; benzene / Heating
2: 90 percent / BF3*Et2O / ethyl acetate / 25 °C
View Scheme
74242-86-7

Diphenylmethyl-2-(3R,4R-3-benzamido-4-chlor-2-oxo-azetidin-1-yl)-3-chlormethyl-3-butenoat

67977-91-7

(2R,6R,7R)-7-Benzoylamino-3-methylene-8-oxo-5-oxa-1-aza-bicyclo[4.2.0]octane-2-carboxylic acid benzhydryl ester

Conditions
ConditionsYield
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
69780-18-3

6-epipenicillin sulfoxide

67977-91-7

(2R,6R,7R)-7-Benzoylamino-3-methylene-8-oxo-5-oxa-1-aza-bicyclo[4.2.0]octane-2-carboxylic acid benzhydryl ester

Conditions
ConditionsYield
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
67977-91-7

(2R,6R,7R)-7-Benzoylamino-3-methylene-8-oxo-5-oxa-1-aza-bicyclo[4.2.0]octane-2-carboxylic acid benzhydryl ester

77945-44-9, 112136-32-0

(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
ConditionsYield
With perchloric acid; trichloroisocyanuric acid In acetone at 25℃;100%
67977-91-7

(2R,6R,7R)-7-Benzoylamino-3-methylene-8-oxo-5-oxa-1-aza-bicyclo[4.2.0]octane-2-carboxylic acid benzhydryl ester

68314-20-5

(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
ConditionsYield
With triethylamine In dichloromethane at 25℃; for 1h;
Raw Materials
67977-61-1
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