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120788-07-0

Basic Information
CAS No.: 120788-07-0
Name: Sulopenem
Article Data: 5
Molecular Structure:
Molecular Structure of 120788-07-0 (Sulopenem)
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
Synthetic route
770673-33-1

(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

120788-07-0

(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
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 25℃; for 18h; Inert atmosphere;72%
120788-06-9

2-Chloroallyl (5R,6S)-6-(1(R)-hydroxyethyl)-2-<(1(R)-oxo-3(S)-thiolanyl)thio>-2-penem-3-carboxylate

120788-07-0

(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
ConditionsYield
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;
120735-10-6, 120735-20-8, 126688-47-9

3(S)-thiolane 1(R)-oxide sodium salt

120788-07-0

(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
ConditionsYield
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
112206-93-6, 112295-83-7, 115793-24-3, 142507-63-9

(3S,4R)-3-<(1R)-1-<(Dimethyl-tert-butylsilyl)oxy>ethyl>-4-<<<(1(R)-oxo-3(S)-thiolanyl)thio>thiocarbonyl>thio>-2-azetidinone

120788-07-0

(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
ConditionsYield
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
120788-05-8

2-Chloroallyl (5R,6S)-6-<1(R)-<(dimethyl-tert-butylsilyl)oxy>ethyl>-2-<(1(R)-oxo-3(S)-thiolanyl)thio>-2-penem-3-carboxylate

120788-07-0

(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
ConditionsYield
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
120788-04-7

(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

120788-07-0

(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
ConditionsYield
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

C15H29NO2S3Si

120788-07-0

(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
ConditionsYield
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
1392406-54-0

allyl 2-((3R,4S)-3-((R)-1-((tert-butyldimethylsilyl)oxy)ethyl)-2-oxo-4-(((propylthio)carbonothioyl)thio)azetidin-1-yl)-2-oxoacetate

120788-07-0

(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
ConditionsYield
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
93603-76-0

(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

120788-07-0

(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
ConditionsYield
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
1392406-55-1

(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

120788-07-0

(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
ConditionsYield
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
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