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CAS No.: | 74288-40-7 |
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Name: | p-Nitrobenzyl-6-(1-hydroxyethyl)-1-azabicyclo(3.2.0)heptane-3,7-dione-2-carboxylate |
Article Data: | 12 |
Molecular Structure: | |
Formula: | C16H16N2O7 |
Molecular Weight: | 348.312 |
Synonyms: | 1-Azabicyclo[3.2.0]heptane-2-carboxylicacid, 6-(1-hydroxyethyl)-3,7-dioxo-, (4-nitrophenyl)methyl ester, [5R-[5a,6a(R*)]]-;ADC 13;p-Nitrobenzyl(5R,6S)-6-((1R)-1-hydroxyethyl)-2-oxocarbapenam-3-carboxylate;p-Nitrobenzyl-6-(1-hydroxyethyl)-1-azabicyclo(3.2.0)heptane-3,7-dione-2-carboxylate; |
EINECS: | 616-072-7 |
Density: | 1.56 g/cm3 |
Melting Point: | 108-110oC |
Boiling Point: | 607.5 °C at 760 mmHg |
Flash Point: | 321.2 °C |
Appearance: | White to off-white powder |
PSA: | 129.73000 |
LogP: | 0.64830 |
(3S,4R)-3-[(R)-1-hydroxyethyl)-4-[3-(4-nitrobenzyl)oxycarbonyl-2-oxo-3-diazopropyl]azetidin-2-one
(5R,6S)-6-[(R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid p-nitrobenzyl ester
Conditions | Yield |
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With dirhodium tetraacetate In toluene at 80℃; for 2.5h; Cyclization; | |
rhodium (II) octanoate dimer In dichloromethane for 4 - 5h; Heating / reflux; | |
With nitrogen; rhodium(II) acetate In benzene |
(3S,4R)-3-[(R)-1-hydroxyethyl)-4-[3-(4-nitrobenzyl)oxycarbonyl-2-oxo-3-diazopropyl]azetidin-2-one
(5R,6S)-6-[(R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid p-nitrobenzyl ester
Conditions | Yield |
---|---|
In toluene |
(5R,6S)-6-[(R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid p-nitrobenzyl ester
Conditions | Yield |
---|---|
With nitrogen; rhodium(II) acetate In benzene |
(3S,4R)-benzyl N-(p-toluenesulfonyl)-3-((R)-1-(tert-butyldimethylsilyloxy)ethyl)-azetidin-2-one-4-carboxylate
(5R,6S)-6-[(R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid p-nitrobenzyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: samarium diiodide; samarium; isopropyl alcohol 2: 10% palladium on activated charcoal; hydrogen / tetrahydrofuran 3: lead(IV) tetraacetate / N,N-dimethyl-formamide 4: zinc(II) chloride / dichloromethane 5: hydrogenchloride; methanol 6: dirhodium tetraacetate / toluene View Scheme |
(3S,4R)-benzyl 3-((R)-1-(tert-butyldimethylsilyloxy)ethyl)-azetidin-2-one-4-carboxylate
(5R,6S)-6-[(R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid p-nitrobenzyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 10% palladium on activated charcoal; hydrogen / tetrahydrofuran 2: lead(IV) tetraacetate / N,N-dimethyl-formamide 3: zinc(II) chloride / dichloromethane 4: hydrogenchloride; methanol 5: dirhodium tetraacetate / toluene View Scheme |
(3R,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one
(5R,6S)-6-[(R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid p-nitrobenzyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: zinc(II) chloride / dichloromethane 2: hydrogenchloride; methanol 3: dirhodium tetraacetate / toluene View Scheme |
4-nitrobenzyl 3-((tert-butyldimethylsilyl)oxy)-2-diazobut-3-enoate
(5R,6S)-6-[(R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid p-nitrobenzyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: zinc(II) chloride / dichloromethane 2: hydrogenchloride; methanol 3: dirhodium tetraacetate / toluene View Scheme |
(3S,4R)-3-<(R)-1'-(dimethyl-t-butylsilyloxy)ethyl>-4-oxoazetidin-2-carboxylic acid
(5R,6S)-6-[(R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid p-nitrobenzyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: lead(IV) tetraacetate / N,N-dimethyl-formamide 2: zinc(II) chloride / dichloromethane 3: hydrogenchloride; methanol 4: dirhodium tetraacetate / toluene View Scheme |
(3S,4R)-3-[(1R)-(tert-butyldimethyl-silyloxy)ethyl]-4-[3-(4-nitrobenzyloxy)carbonyl-2-oxo-3-diazopropyl]azetidin-2-one
(5R,6S)-6-[(R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid p-nitrobenzyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: hydrogenchloride; methanol 2: dirhodium tetraacetate / toluene View Scheme |
(5R,6S)-6-[(R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid p-nitrobenzyl ester
ethyl 2-sulfanylacetate
Conditions | Yield |
---|---|
Stage #1: (5R,6S)-6-[(R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid p-nitrobenzyl ester With N-ethyl-N,N-diisopropylamine; chlorophosphoric acid diphenyl ester In acetonitrile at 0℃; for 0.75h; Stage #2: ethyl 2-sulfanylacetate With N-ethyl-N,N-diisopropylamine In acetonitrile at 0℃; for 1h; | 74% |
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Molecular Structure of P-Nitrobenzyl-6-(1-hydroxyethyl)-1-azabicyclo(3.2.0)heptane-3,7-dione-2-carboxylate (CAS NO.74288-40-7):
Empirical Formula: C16H16N2O7
Molecular Weight: 348.3074
Index of Refraction: 1.631
Surface Tension: 71.9 dyne/cm
Density: 1.5 g/cm3
Flash Point: 317.4 °C
Enthalpy of Vaporization: 94.09 kJ/mol
Boiling Point: 601.3 °C at 760 mmHg
Vapour Pressure: 2.63E-15 mmHg at 25°C
Product Categories: (intermediate of imipenem,panipenem);Intermediates & Fine Chemicals; Pharmaceuticals
The usage of P-Nitrobenzyl-6-(1-hydroxyethyl)-1-azabicyclo(3.2.0)heptane-3,7-dione-2-carboxylate (CAS NO.74288-40-7) is as imipenem intermediate.
P-Nitrobenzyl-6-(1-hydroxyethyl)-1-azabicyclo(3.2.0)heptane-3,7-dione-2-carboxylate ,its cas register number is 73323-65-6. It also can be called 1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-(1-hydroxyethyl)-3,7-dioxo-, (4-nitrophenyl)methyl ester, (5R,6S)- ; 1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[(1R)-1-hydroxyethyl]-3,7-dioxo-, (4-nitrophenyl)methyl ester, (5R,6S)- ; (1'R,5R,6S)-6-(1-Hydroxy-ethyl)-3,7-dioxo-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl ester and so on.