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Biapenem
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Name

Biapenem

 EINECS 204-352-8
CAS No. 120410-24-4 Density N/A
PSA 127.67000 LogP -1.95710
Solubility N/A Melting Point 265-271°C (dec.)
Formula C15H18N4O4S Boiling Point N/A
Molecular Weight 350.398 Flash Point N/A
Transport Information N/A Appearance White to light yellow powder
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 120410-24-4 (Biapenem) Hazard Symbols N/A
Synonyms

[(4R,5R,6S)-3-(3,5-diaza-1-azoniabicyclo[3.3.0]octa-1,3-dien-7-ylsulfanyl)-6-(1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-en-2-yl]-hydroxy-methanolate;5H-Pyrazolo(1,2-a)(1,2,4)triazol-4-ium, 6-((2-carboxy-6-(1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo(3.2.0)hept-2-en-3-yl)thio)-6,7-dihydro-, hydroxide, inner salt, (4R-(4alpha,5beta,6beta(R*)))-;Omegacin (TN);6-[(4R,5S,6S)-2-carboxy-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-l-azabicyco-[ 3 . 2 . 0 ]hept-2-ene-3-yl]thio-6,7-dihydro-5H-pyrazolo-[1,2-a][1,2,4]t-riazol-4-ium hydroxideinner salt;Taizhou hikong chemical sell Biapenem;5H-Pyrazolo[1,2-a][1,2,4]triazol-4-ium,6- [[(4R,5S,6S)-2-carboxy-6-[(1R)-1-hydroxyethyl]- 4-methyl-7-oxo-1-azabicyclo[3.2.0]- hept-2-en-3-yl]thio]-6,7-dihydro-,inner salt;Omegacin;Name: Biapenem;

Article Data 5

Biapenem Synthetic route

6-[[(4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-2-(((4-nitrobenzyl)oxy)carbonyl)-7-oxo-1-azabicyclo[3.2.0]hept-2-en-3-yl]thio]-6,7-dihydro-5H-pyrazolo[1,2-a][1,2,4]triazol-4-ium chloride

120410-24-4

biapenem

Conditions
ConditionsYield
With zinc In phosphate buffer at 20℃; for 1h; pH=5.6; Reduction;80%
With 2,6-dimethylpyridine; palladium-carbon; hydrogen In tetrahydrofuran; water; ethyl acetate at 30 - 35℃; under 7500.75 - 9000.9 Torr; for 2h; Large scale;75%
93711-81-0, 90776-59-3

(4-nitrophenyl)methyl (4R,5R,6S)-3-[(diphenoxyphosphinyl)oxy]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

6-mercapto-6,7-dihydro-5H-pyrazolo<1,2-a><1,2,4>triazolium chloride

120410-24-4

biapenem

Conditions
ConditionsYield
With potassium phosphate buffer; hydrogen; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal 1.) DMF, MeOH, 0 deg C to 5 deg C, 25 min, 2.) n-butanol, EtOAc, water, 3.2 kg/cm2, 2 h; Yield given. Multistep reaction;

4-[(4R,5S,6S)-2-Carboxy-6-((R)-1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-en-3-ylsulfanyl]-pyrazolidine-1,2-dicarboxylic acid

120410-24-4

biapenem

Conditions
ConditionsYield
With sodium hydroxide; ethyl formimidate hydrochloride In tetrahydrofuran; water at 0℃; for 0.0833333h; Yield given;

6-mercapto-6,7-dihydro-5H-pyrazolo<1,2-a><1,2,4>triazolium chloride

120410-24-4

biapenem

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 91 percent / diisopropylethylamine / acetonitrile; acetone; dimethylformamide / 2 h / 0 °C
2: 80 percent / zinc / aq. phosphate buffer / 1 h / 20 °C / pH 5.6
View Scheme

bis(6,7-dihydro-5H-pyrazolo[1,2-a][1,2,4]triazolium-6-yl) disulfide dichloride

120410-24-4

biapenem

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 70 percent / n-Bu3P / tetrahydrofuran; H2O / 1 h / 0 °C
2: 91 percent / diisopropylethylamine / acetonitrile; acetone; dimethylformamide / 2 h / 0 °C
3: 80 percent / zinc / aq. phosphate buffer / 1 h / 20 °C / pH 5.6
View Scheme

6-(p-methoxybenzylthio)-6,7-dihydro-5H-pyrazolo<1,2-a><1,2,4>triazolium chloride

120410-24-4

biapenem

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 73.5 percent / TFA, anisole, trifluoromethanesulfonic acid / 1 h / 0 - 5 °C
2: 1.) N,N-diisopropylethylamine, 2.) H2, potassium phosphate buffer / 2.) 20percent Pd/C / 1.) DMF, MeOH, 0 deg C to 5 deg C, 25 min, 2.) n-butanol, EtOAc, water, 3.2 kg/cm2, 2 h
View Scheme
93711-81-0, 90776-59-3

(4-nitrophenyl)methyl (4R,5R,6S)-3-[(diphenoxyphosphinyl)oxy]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

120410-24-4

biapenem

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: diisopropylethylamine / acetonitrile / 0.67 h / -5 °C
2: H2 / 10percent Pd / C / tetrahydrofuran; H2O / 1.67 h / 3040 Torr / Ambient temperature
3: ethyl formimidate hydrochloride, 1N NaOH / tetrahydrofuran; H2O / 0.08 h / 0 °C
View Scheme
104873-15-6

4-nitrobenzyl (4R,5R,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-3,7-dioxo-1-azabicyclo[3.2.0]-heptane-2-carboxylate

120410-24-4

biapenem

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: diisopropylethylamine / acetonitrile / 0.5 h / -10 °C
2: diisopropylethylamine / acetonitrile / 0.67 h / -5 °C
3: H2 / 10percent Pd / C / tetrahydrofuran; H2O / 1.67 h / 3040 Torr / Ambient temperature
4: ethyl formimidate hydrochloride, 1N NaOH / tetrahydrofuran; H2O / 0.08 h / 0 °C
View Scheme
120764-68-3

p-Nitrobenzyl (1R,5S,6S)-2-<<(N,N-Bis(p-nitrobenzyloxycarbonyl)pyrazolidin-4-yl>thio>-6-<(1R)-1-hydroxyethyl>-1-methylcarbapen-2-em-3-carboxylate

120410-24-4

biapenem

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: H2 / 10percent Pd / C / tetrahydrofuran; H2O / 1.67 h / 3040 Torr / Ambient temperature
2: ethyl formimidate hydrochloride, 1N NaOH / tetrahydrofuran; H2O / 0.08 h / 0 °C
View Scheme

p-nitrobenzyl (4R,5S,6S)-3-(6,7-dihydro-5H-pyrazolo[1,2-a][1,2,4]triazol-8-ium-6-ylsulfanyl)-6-(1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

120410-24-4

biapenem

Conditions
ConditionsYield
With palladium on activated charcoal; hydrogen In tetrahydrofuran at 5 - 10℃; pH=7-8;

Biapenem Chemical Properties

Structure of Biapenem (CAS NO.120410-24-4):
                         

IUPAC Name: (4R,5S,6S)-3-(6,7-dihydro-5H-pyrazolo[1,2-a][1,2,4]triazol-8-ium-6-ylsulfanyl)-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
Molecular Formula: C15H18N4O4S
Molecular Weight: 350.39 g/mol
CAS: 120410-24-4
H bond acceptors: 8
H bond donors: 2
Freely Rotating Bonds: 5
Polar Surface Area: 113.84 Å2
Appearance: White to light yellow powder
Product Category of Biapenem (CAS NO.120410-24-4): API; chiral; Antibacterial; pharmaceutical intermediates
InChI
InChI=1/C15H18N4O4S/c1-7-11-10(8(2)20)14(21)19(11)12(15(22)23)13(7)24-9-3-17-5-16-6-18(17)4-9/h5-11,20H,3-4H2,1-2H3/t7-,8-,10-,11-/m1/s1
Smiles
C=1([C@H](C)[C@@H]2[C@H](C(N2C1C(=O)[O-])=O)[C@@H](C)O)SC1C[n+]2cncn2C1

Biapenem Specification

 Biapenem , its cas register number is 120410-24-4. It also can be called 6-[[(4R,5S,6S)-2-Carboxy-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-en-3-yl]thio]-6,7-dihydro-5H-pyrazolo[1,2-a][1,2,4]triazol-4-ium inner salt ; (4R,5S,6S)-3-(6,7-dihydro-5H-pyrazolo[1,2-a][1,2,4]triazol-4-ium-6-ylthio)-6-((R)-1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate ; 6-[[(4R,5S,6S)-2-Carboxylato-6β-[(1R)-1-hydroxyethyl]-4α-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-en-3-yl]thio]-6,7-dihydro-5H-pyrazolo[1,2-a]-s-triazol-4-ium ; 6-[[(4R,5S,6S)-2-Carboxylato-6β-[(R)-1-hydroxyethyl]-4α-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-en-3-yl]thio]-6,7-dihydro-5H-pyrazolo[1,2-a][1,2,4]triazol-4-ium ; 6-[[(4R,5β)-2-Carboxylato-4α-methyl-6β-[(R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-en-3-yl]thio]-6,7-dihydro-5H-pyrazolo[1,2-a][1,2,4]triazol-4-ium . Biapenem (CAS NO.120410-24-4) is a carbapenem antibiotic and can be used in vitro activity against anaerobes.

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