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CAS No.: | 120788-07-0 |
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Name: | Sulopenem |
Article Data: | 5 |
Molecular Structure: | |
Formula: | C12H15 N O5 S3 |
Molecular Weight: | 349.453 |
Synonyms: | 4-Thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylicacid, 6-(1-hydroxyethyl)-7-oxo-3-[(tetrahydro-3-thienyl)thio]-, S-oxide,[5R-[3(1R*,3S*),5a,6a(R*)]]-; (S)-CP 70429;4-Thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid,6-(1-hydroxyethyl)-7-oxo-3-[(tetrahydro-1-oxido-3-thienyl)thio]-,[5R-[3(1R*,3S*),5a,6a(R*)]]-; CP 70429; Sulopenem |
Density: | 1.74g/cm3 |
Boiling Point: | 693.1°Cat760mmHg |
Flash Point: | 373°C |
PSA: | 164.72000 |
LogP: | 1.21000 |
(3S)-3-({(5R,6S)-6-[(1R)-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl]-2-carboxy-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-en-3 yl}sulfanyl)tetrahydrothiophenium-1-olate
(3S)-3-({(5R, 6S)-2-carboxy-6-[(1R)-1-hydroxyethyl]-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-en-3-yl}sulfanyl)tetrahydrothiophenium-1-olate
Conditions | Yield |
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With tetrabutyl ammonium fluoride In tetrahydrofuran at 25℃; for 18h; Inert atmosphere; | 72% |
2-Chloroallyl (5R,6S)-6-(1(R)-hydroxyethyl)-2-<(1(R)-oxo-3(S)-thiolanyl)thio>-2-penem-3-carboxylate
(3S)-3-({(5R, 6S)-2-carboxy-6-[(1R)-1-hydroxyethyl]-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-en-3-yl}sulfanyl)tetrahydrothiophenium-1-olate
Conditions | Yield |
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With hydrogenchloride; tetrakis(triphenylphosphine) palladium(0); triphenylphosphine; sodium 2-ethylhexanoic acid 1.) rt, 2.) H2O, 0 - 5 deg C, 45 min; Yield given. Multistep reaction; |
3(S)-
(3S)-3-({(5R, 6S)-2-carboxy-6-[(1R)-1-hydroxyethyl]-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-en-3-yl}sulfanyl)tetrahydrothiophenium-1-olate
Conditions | Yield |
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Multi-step reaction with 5 steps 1: propan-2-ol; CS2 / 0.5 h / 3 °C 2: 98 percent / N,N-diisopropylethylamine / CH2Cl2 / 0.25 h / -55 - -50 °C 3: 56 percent / P(OEt)3 / CHCl3 / 10 h / Heating 4: 83 percent / glacial acetic acid, tetrabutylammonium fluoride / tetrahydrofuran / 16 h / Ambient temperature 5: 1.) triphenylphosphine, tetrakis(triphenylphosphine)palladium(0), sodium 2-ethylhexamoate, 2.) 1 N HCl / 1.) rt, 2.) H2O, 0 - 5 deg C, 45 min View Scheme | |
Multi-step reaction with 5 steps 1: acetone; tetrahydrofuran / 0.5 h / 0 °C 2: 98 percent / N,N-diisopropylethylamine / CH2Cl2 / 0.25 h / -55 - -50 °C 3: 56 percent / P(OEt)3 / CHCl3 / 10 h / Heating 4: 83 percent / glacial acetic acid, tetrabutylammonium fluoride / tetrahydrofuran / 16 h / Ambient temperature 5: 1.) triphenylphosphine, tetrakis(triphenylphosphine)palladium(0), sodium 2-ethylhexamoate, 2.) 1 N HCl / 1.) rt, 2.) H2O, 0 - 5 deg C, 45 min View Scheme |
(3S,4R)-3-<(1R)-1-<(Dimethyl-tert-butylsilyl)oxy>ethyl>-4-<<<(1(R)-oxo-3(S)-thiolanyl)thio>thiocarbonyl>thio>-2-azetidinone
(3S)-3-({(5R, 6S)-2-carboxy-6-[(1R)-1-hydroxyethyl]-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-en-3-yl}sulfanyl)tetrahydrothiophenium-1-olate
Conditions | Yield |
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Multi-step reaction with 4 steps 1: 98 percent / N,N-diisopropylethylamine / CH2Cl2 / 0.25 h / -55 - -50 °C 2: 56 percent / P(OEt)3 / CHCl3 / 10 h / Heating 3: 83 percent / glacial acetic acid, tetrabutylammonium fluoride / tetrahydrofuran / 16 h / Ambient temperature 4: 1.) triphenylphosphine, tetrakis(triphenylphosphine)palladium(0), sodium 2-ethylhexamoate, 2.) 1 N HCl / 1.) rt, 2.) H2O, 0 - 5 deg C, 45 min View Scheme |
2-Chloroallyl (5R,6S)-6-<1(R)-<(dimethyl-tert-butylsilyl)oxy>ethyl>-2-<(1(R)-oxo-3(S)-thiolanyl)thio>-2-penem-3-carboxylate
(3S)-3-({(5R, 6S)-2-carboxy-6-[(1R)-1-hydroxyethyl]-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-en-3-yl}sulfanyl)tetrahydrothiophenium-1-olate
Conditions | Yield |
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Multi-step reaction with 2 steps 1: 83 percent / glacial acetic acid, tetrabutylammonium fluoride / tetrahydrofuran / 16 h / Ambient temperature 2: 1.) triphenylphosphine, tetrakis(triphenylphosphine)palladium(0), sodium 2-ethylhexamoate, 2.) 1 N HCl / 1.) rt, 2.) H2O, 0 - 5 deg C, 45 min View Scheme |
(3S,4R)-N-<<(2-Chlorallyl)oxy>oxalyl>-3-<1(R)-1-<(dimethyl-tert-butylsilyl)oxy>ethyl>-4-<<<(1(R)-oxo-3(S)-thiolanyl)thio>thiocarbonyl>thio>-2-azetidinone
(3S)-3-({(5R, 6S)-2-carboxy-6-[(1R)-1-hydroxyethyl]-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-en-3-yl}sulfanyl)tetrahydrothiophenium-1-olate
Conditions | Yield |
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Multi-step reaction with 3 steps 1: 56 percent / P(OEt)3 / CHCl3 / 10 h / Heating 2: 83 percent / glacial acetic acid, tetrabutylammonium fluoride / tetrahydrofuran / 16 h / Ambient temperature 3: 1.) triphenylphosphine, tetrakis(triphenylphosphine)palladium(0), sodium 2-ethylhexamoate, 2.) 1 N HCl / 1.) rt, 2.) H2O, 0 - 5 deg C, 45 min View Scheme |
(3S)-3-({(5R, 6S)-2-carboxy-6-[(1R)-1-hydroxyethyl]-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-en-3-yl}sulfanyl)tetrahydrothiophenium-1-olate
Conditions | Yield |
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Multi-step reaction with 6 steps 1: triethylamine / mineral oil; tert-butyl methyl ether / -10 - 20 °C 2: methyldiethoxyphosphine / toluene / 4 h / 90 °C / Inert atmosphere 3: urea hydrogen peroxide adduct; 1,1,1,3',3',3'-hexafluoro-propanol / toluene / 20 - 25 °C 4: triethylamine / Isopropyl acetate; n-heptane / 2 h / -20 - 5 °C 5: palladium diacetate; triethyl phosphite; sodium benzenesulfonate / tetrahydrofuran; water / 4 h / 25 °C / Inert atmosphere 6: tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 25 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 6 steps 1: triethylamine / mineral oil; tert-butyl methyl ether / -10 - 20 °C 2: methyldiethoxyphosphine / toluene / Heating 3: urea hydrogen peroxide adduct; 1,1,1,3',3',3'-hexafluoro-propanol / toluene / 20 - 25 °C 4: triethylamine / Isopropyl acetate; n-heptane / 2 h / -20 - 5 °C 5: palladium diacetate; triethyl phosphite; sodium benzenesulfonate / tetrahydrofuran; water / 4 h / 25 °C / Inert atmosphere 6: tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 25 °C / Inert atmosphere View Scheme |
allyl 2-((3R,4S)-3-((R)-1-((tert-butyldimethylsilyl)oxy)ethyl)-2-oxo-4-(((propylthio)carbonothioyl)thio)azetidin-1-yl)-2-oxoacetate
(3S)-3-({(5R, 6S)-2-carboxy-6-[(1R)-1-hydroxyethyl]-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-en-3-yl}sulfanyl)tetrahydrothiophenium-1-olate
Conditions | Yield |
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Multi-step reaction with 5 steps 1: methyldiethoxyphosphine / toluene / 4 h / 90 °C / Inert atmosphere 2: urea hydrogen peroxide adduct; 1,1,1,3',3',3'-hexafluoro-propanol / toluene / 20 - 25 °C 3: triethylamine / Isopropyl acetate; n-heptane / 2 h / -20 - 5 °C 4: palladium diacetate; triethyl phosphite; sodium benzenesulfonate / tetrahydrofuran; water / 4 h / 25 °C / Inert atmosphere 5: tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 25 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 5 steps 1: methyldiethoxyphosphine / toluene / Heating 2: urea hydrogen peroxide adduct; 1,1,1,3',3',3'-hexafluoro-propanol / toluene / 20 - 25 °C 3: triethylamine / Isopropyl acetate; n-heptane / 2 h / -20 - 5 °C 4: palladium diacetate; triethyl phosphite; sodium benzenesulfonate / tetrahydrofuran; water / 4 h / 25 °C / Inert atmosphere 5: tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 25 °C / Inert atmosphere View Scheme |
(5R,6S)-allyl 6-((R)-1-(tert-butyldimethylsilyloxy)ethyl)-7-oxo-3-(propylthio)-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
(3S)-3-({(5R, 6S)-2-carboxy-6-[(1R)-1-hydroxyethyl]-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-en-3-yl}sulfanyl)tetrahydrothiophenium-1-olate
Conditions | Yield |
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Multi-step reaction with 4 steps 1: urea hydrogen peroxide adduct; 1,1,1,3',3',3'-hexafluoro-propanol / toluene / 20 - 25 °C 2: triethylamine / Isopropyl acetate; n-heptane / 2 h / -20 - 5 °C 3: palladium diacetate; triethyl phosphite; sodium benzenesulfonate / tetrahydrofuran; water / 4 h / 25 °C / Inert atmosphere 4: tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 25 °C / Inert atmosphere View Scheme |
(5R,6S)-allyl 6-((R)-1-(tert-butyldimethylsilyloxy)ethyl)-7-oxo-3-(propylsulfinyl)-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
(3S)-3-({(5R, 6S)-2-carboxy-6-[(1R)-1-hydroxyethyl]-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-en-3-yl}sulfanyl)tetrahydrothiophenium-1-olate
Conditions | Yield |
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Multi-step reaction with 3 steps 1: triethylamine / Isopropyl acetate; n-heptane / 2 h / -20 - 5 °C 2: palladium diacetate; triethyl phosphite; sodium benzenesulfonate / tetrahydrofuran; water / 4 h / 25 °C / Inert atmosphere 3: tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 25 °C / Inert atmosphere View Scheme |