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(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 |
---|---|
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 |
---|---|
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)-<thio>thiolane 1(R)-oxide sodium salt
(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 |
---|---|
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 |
---|---|
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 |
---|---|
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 |
---|---|
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 |
---|---|
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 |
---|---|
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 |
---|---|
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 |
---|---|
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 |
4-(bromomethyl)-5-(2-methylpropyl)-1,3-dioxol-2-one
(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
(5-(2-methylpropyl)-2-oxo-1,3-dioxol-4-yl)methyl (5R,6S)-6-[(1R)-1-hydroxyethyl]-7-oxo-3-[[(1R,3S)-tetrahydro-1-oxido-3-thienyl]thio]-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In acetone at 25℃; for 9h; | 69% |
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