Name:4-nitrobenzyl (5R,6S)-6-[(1R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylate CAS:74288-40-7 Molecular structure : Molecular Formula:C16H16N2O7 Molecular weight:348.32 Melting point:109~ 114°C Appearan
Cas:74288-40-7
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inquiryWelcome to Simagchem, your partner in China as a premier supply of bulk specialty chemicals for industry and life science. We introduce experienced quality product and exceptional JIT service with instant market intelligence in China to benefit our
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inquiryB-CHETO English name: B-CHETO Chemical name: [5R-(5α,6α(R*))]-6-(1-hydroxyethyl)-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid (4-nitrophenyl)methyl ester Category invol
The above product is Ality Chemical's strong item with best price, good quality and fast supply. Ality Chemical has been focusing on the research and production of this field for over 14 years. At the same time, we are always committed to providi
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inquiryCangzhou Enke Pharma Tech Co.,ltd. is located in Cangzhou City, Hebei province ,where is a famous petroleum chemical industry city in China. Enke Pharma a high-tech enterprise ,and we are dedicated to developing and manufacturing new ap
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inquiryAs a leading manufacturer and supplier of chemicals in China, DayangChem not only supply popular chemicals, but also DayangChem’s R&D center offer custom synthesis according to the contract research and development services for the fine c
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inquirySleeping pills and stability.This product is white or white crystalline powder;Odourless and slightly bitter taste.Almost insoluble in water, soluble in hydrochloric acid.In acid or alkali and heat hydrolysis, oral drug under the action of gastric
Cas:74288-40-7
Min.Order:10000 Gram
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inquiryOur advantages: 1. All inquiries will be replied within 12 hours. 2. Dedication to quality, supply & service. 3. Strictly on selecting raw materials. 4. Reasonable & competitive price, fast lead time. 5. Sample is available for your eva
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inquiryAdvantage : LIDE PHARMACEUTICALS LTD. is a mid-small manufacturing-type enterprise, engaged in pharmaceutical intermediates of R&D, custom-made and production, and also involving trading chemicals for export. We have established the R&
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inquirynglish name: Imipenem intermediate ADC-13 Synonyms: 6-[(1R)-1-Hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid (5R,6S)-(4-nitrophenyl)methyl ester; ADC 13 CAS NO.:
Appearance white or almost white crystalline powder Assay,on dry base 98%min Purity 98%min Melting point
Cas:74288-40-7
Min.Order:1 Gram
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inquiry1. Guaranteed purity; 2. Large quantity in stock; 3. Largest manufacturer; 4. Best service after shipment with email; 5. High quality & competitive price; Appearance:white solid Storage:Store in sealed containers at cool & dry
Cas:74288-40-7
Min.Order:100 Gram
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inquiry74288-40-7 Package:As per buy's request ISO/SGS/REACH Certificate Fast Delivery Package:1kg-200KG Drum With Pallet Port:China Main Port
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Cas:74288-40-7
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inquiryp-Nitrobenzyl-6-(1-hydroxyethyl)-1-azabicyclo(3.2.0)heptane-3,7-dione-2-carboxylate CAS:74288-40-7 Qingdao Belugas Import and Export Co., Ltd. is a scientific and technological company integrating research and development, production and trade of ch
Cas:74288-40-7
Min.Order:1 Gram
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inquiryHello, dear friend! I'm Hansen and Allen from China. Welcome to my lookchem mall! The following is a brief introduction of our company's products and services. If you are interested in our products, please contact us by emai
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inquiryCompany Introduction 1. Established in 2005, with two independent business divisions: Fine chemicals division; Pharmaceutical division. 2. Main product: Optical brightener Textile auxiliary Dye stuff Pigments
Cas:74288-40-7
Min.Order:1 Gram
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Type:Lab/Research institutions
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inquiryA substitute for perfluorooctanoic acid, mainly used as a surfactant, dispersant, additive, etc Appearance:White solid or Colorless liquid Purity:99.3 % We will ship the goods in a timely manner as required We can provide relevant documents acc
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Min.Order:100 Gram
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inquiryEstablished in May 2015, TaiChem Ltd. is initially invested by a British research and development company and started by PhDs back from aboard. The company is registered in China Medical City (CMC), Taizhou, Jiangsu Province, and the production site
Cas:74288-40-7
Min.Order:10 Gram
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Type:Lab/Research institutions
inquiry(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 |
---|---|
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% |
(5R,6S)-6-[(R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid p-nitrobenzyl ester
chlorophosphoric acid diphenyl ester
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; chlorophosphoric acid diphenyl ester With N-ethyl-N,N-diisopropylamine In acetonitrile for 2h; Substitution; Stage #2: (S)-4-mercapto-2-oxoppyrrolidine With N-ethyl-N,N-diisopropylamine In acetonitrile for 1h; Substitution; | 67% |
t-butyldimethylsiyl triflate
(5R,6S)-6-[(R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid p-nitrobenzyl ester
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 trifluoromethylsulfonic anhydride; triethylamine In dichloromethane at -78℃; for 0.5h; Inert atmosphere; Stage #2: t-butyldimethylsiyl triflate In dichloromethane at -78℃; for 0.5h; Inert atmosphere; Stage #3: (E)-(4-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)phenyl)methanol With tris-(dibenzylideneacetone)dipalladium(0); potassium hydroxide In dichloromethane; water; N,N-dimethyl-formamide at -78 - 30℃; for 1h; Inert atmosphere; | 59% |
p-hydroxymethylphenylboronic acid
Triethylsilyl trifluoromethanesulfonate
(5R,6S)-6-[(R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid p-nitrobenzyl ester
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 trifluoromethylsulfonic anhydride; triethylamine In dichloromethane at -78℃; for 0.5h; Inert atmosphere; Stage #2: triethylsilyl trifluoromethyl sulfonate In dichloromethane at -78℃; for 1h; Inert atmosphere; Stage #3: p-hydroxymethylphenylboronic acid With tris-(dibenzylideneacetone)dipalladium(0); potassium hydroxide In water; N,N-dimethyl-formamide at -78 - 30℃; for 1.5h; Inert atmosphere; | 33% |
trifluoromethylsulfonic anhydride
trimethylsilyl trifluoromethanesulfonate
tributylethynyltin
(5R,6S)-6-[(R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid p-nitrobenzyl ester
Conditions | Yield |
---|---|
Stage #1: trifluoromethylsulfonic anhydride; (5R,6S)-6-[(R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid p-nitrobenzyl ester With diisopropylamine In tetrahydrofuran at -78℃; for 0.25h; Addition; Stage #2: trimethylsilyl trifluoromethanesulfonate With triethylamine In tetrahydrofuran at -78℃; for 0.333333h; Etherification; Stage #3: tributylethynyltin With trifuran-2-yl-phosphane; tris-(dibenzylideneacetone)dipalladium(0); zinc(II) chloride In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; diethyl ether at 20℃; for 2h; Addition; Stille coupling; | 32% |
cis-1-cyano-4-mercaptocyclohexane
(5R,6S)-6-[(R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid p-nitrobenzyl ester
p-nitrobenzyl (6S)-<(1R)-hydroxyethyl>-2--(5R)-carbapen-2-em-3-carboxylate
Conditions | Yield |
---|---|
With diisopropylamine; chlorophosphoric acid diphenyl ester 1) CH3CN, 0 to 5 deg C, 1 h, 2) CH3CN, RT, 20 h; Yield given. Multistep reaction; |
cis-3-mercaptocyclopentanecarboxamide
(5R,6S)-6-[(R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid p-nitrobenzyl ester
p-nitrobenzyl (6S)-<(1R)-hydroxyethyl>-2--(5R)-carbapen-2-em-3-carboxylate
Conditions | Yield |
---|---|
With diisopropylamine; chlorophosphoric acid diphenyl ester 1) CH3CN, 0 to 5 deg C, 1 h, 2) DMF, RT, 3 d; Yield given. Multistep reaction; |
cis-4-mercaptocyclohexanecarboxamide
(5R,6S)-6-[(R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid p-nitrobenzyl ester
p-nitrobenzyl (6S)-<(1R)-hydroxyethyl>-2--(5R)-carbapen-2-em-3-carboxylate
Conditions | Yield |
---|---|
With diisopropylamine; chlorophosphoric acid diphenyl ester 1) CH3CN, 0 to 5 deg C, 1 h, 2) DMF, RT, 3 d; Yield given. Multistep reaction; |
cis-3-mercapto-1-(p-nitrobenzyloxycarboxylamino)cyclopentane
(5R,6S)-6-[(R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid p-nitrobenzyl ester
p-nitrobenzyl (6S)-<(1R)-hydroxyethyl>-2--(5R)-carbapen-2-em-3-carboxylate
Conditions | Yield |
---|---|
With diisopropylamine; chlorophosphoric acid diphenyl ester 1) CH3CN, 0 to 5 deg C, 1 h, 2) CH3CN, RT, 20 h; Yield given. Multistep reaction; |
cis-4-mercapto-1-(p-nitrobenzyloxycarbonylamino)cyclohexane
(5R,6S)-6-[(R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid p-nitrobenzyl ester
p-nitrobenzyl (6S)-<(1R)-hydroxyethyl>-2--(5R)-carbapen-2-em-3-carboxylate
Conditions | Yield |
---|---|
With diisopropylamine; chlorophosphoric acid diphenyl ester 1) CH3CN, 0 to 5 deg C, 1 h, 2) CH3CN, RT, 6 d; Yield given. Multistep reaction; |
cis-4-(p-nitrobenzyloxycarbonylaminomethyl)cyclohexylthiol
(5R,6S)-6-[(R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid p-nitrobenzyl ester
p-nitrobenzyl (6S)-<(1R)-hydroxyethyl>-2--(5R)-carbapen-2-em-3-carboxylate
Conditions | Yield |
---|---|
With diisopropylamine; chlorophosphoric acid diphenyl ester 1) CH3CN, 0 to 5 deg C, 1 h, 2) DMF, RT, 6 d; Yield given. Multistep reaction; |
trifluoromethylsulfonic anhydride
(5R,6S)-6-[(R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid p-nitrobenzyl ester
p-nitrobenzyl (5R,6S)-6-[(1R)-1-hydroxyethyl]-2-trifluoromethylsulphonyloxy-carbapen-2-em-3carboxylate
Conditions | Yield |
---|---|
With diisopropylamine In tetrahydrofuran at -70℃; for 0.5h; Addition; Title compound not separated from byproducts; |
(5R,6S)-6-[(R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid p-nitrobenzyl ester
chlorophosphoric acid diphenyl ester
p-nitrobenzyl (5R,6S)-2-diphenoxy phosphoryloxy-6-[(R)-1-hydroxyethyl]-1-carbapen-2-em-3-carboxylate
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In acetonitrile at 0℃; for 1h; Addition; | |
With dmap; N-ethyl-N,N-diisopropylamine In acetonitrile |
p-toluenesulfonylanhydride
(5R,6S)-6-[(R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid p-nitrobenzyl ester
(5R,6S)-6-((R)-1-Hydroxy-ethyl)-7-oxo-3-(toluene-4-sulfonyloxy)-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at -60 - 0℃; |
diazomethane
(5R,6S)-6-[(R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid p-nitrobenzyl ester
Conditions | Yield |
---|---|
In 1,4-dioxane at 20℃; Methylation; |
(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: dioxane / 20 °C 2: H2 / 10 percent Pd/C / ethyl acetate / 0 °C View Scheme |
(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: Et3N / CH2Cl2 / -60 - 0 °C 2: Et3N / CH2Cl2 / 12 h / -70 °C 3: 67 percent / Bu4N(+)Cl(-), K2CO3 / PdCl2(dppf) / tetrahydrofuran; H2O; CH2Cl2 / 1.67 h / 30 °C View Scheme |
(5R,6S)-6-[(R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid p-nitrobenzyl ester
(5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-7-oxo-3-(toluene-4-sulfonyloxy)-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: Et3N / CH2Cl2 / -60 - 0 °C 2: Et3N / CH2Cl2 / 12 h / -70 °C View Scheme |
(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: N,N-diisopropylethylamine / acetonitrile / 1 h / 0 °C 2: N,N-diisopropylethylamine / acetonitrile 3: H2 / 10 percent Pd-C / tetrahydrofuran; aq. phosphate buffer / 2.5 h / 20 °C / pH 7 View Scheme |
(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: N,N-diisopropylethylamine / acetonitrile / 1 h / 0 °C 2: N,N-diisopropylethylamine / acetonitrile View Scheme |
(5R,6S)-6-[(R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid p-nitrobenzyl ester
p-nitrobenzyl (5R,6S)-2-ethynyl-6-[(1R)-1-hydroxyethyl]carbapen-2-em-3-carboxylate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: diisopropylamine / tetrahydrofuran / 0.25 h / -78 °C 1.2: Et3N / tetrahydrofuran / 0.33 h / -78 °C 1.3: 32 percent / tri(2-furyl)phosphine / tris(dibenzylideneacetone)dipalladium; ZnCl2 / 1-methyl-pyrrolidin-2-one; tetrahydrofuran; diethyl ether / 2 h / 20 °C 2.1: 85 percent / AcOH; aq. Bu4NF / tetrahydrofuran / 1.75 h / 0 - 20 °C View Scheme |
(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: diisopropylamine / tetrahydrofuran / 0.5 h / -70 °C 2: Ph3As / ZnCl2, LiCl; tris(dibenzylideneacetone)dipalladium / tetrahydrofuran / 3 h / 20 °C View Scheme |
(5R,6S)-6-[(R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid p-nitrobenzyl ester
(5R,6S)-6-((R)-1-Hydroxy-ethyl)-7-oxo-3-thiazol-5-yl-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: diisopropylamine / tetrahydrofuran / 0.5 h / -70 °C 2: Ph3As / ZnCl2, LiCl; tris(dibenzylideneacetone)dipalladium / tetrahydrofuran / 3 h / 20 °C View Scheme |
(5R,6S)-6-[(R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid p-nitrobenzyl ester
p-Nitrobenzyl-(5R,6S)-6-[(1R)-hydroxyethyl]-2-(1-methylpyrazol-3-yl)-carbapen-2-em-3-carboxylate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: diisopropylamine / tetrahydrofuran / 0.5 h / -70 °C 2: Ph3As / ZnCl2, LiCl; tris(dibenzylideneacetone)dipalladium / tetrahydrofuran / 3 h / 20 °C View Scheme |
(5R,6S)-6-[(R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid p-nitrobenzyl ester
(5R,6S)-6-((R)-1-Hydroxy-ethyl)-3-(3-methyl-isoxazol-5-yl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: diisopropylamine / tetrahydrofuran / 0.25 h / -78 °C 1.2: Et3N / tetrahydrofuran / 0.33 h / -78 °C 1.3: 32 percent / tri(2-furyl)phosphine / tris(dibenzylideneacetone)dipalladium; ZnCl2 / 1-methyl-pyrrolidin-2-one; tetrahydrofuran; diethyl ether / 2 h / 20 °C 2.1: 85 percent / AcOH; aq. Bu4NF / tetrahydrofuran / 1.75 h / 0 - 20 °C 3.1: Et3N / CH2Cl2; hexane / 1 h / 20 °C View Scheme |
(5R,6S)-6-[(R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid p-nitrobenzyl ester
(5R,6S)-6-((R)-1-Hydroxy-ethyl)-3-(3-isopropyl-isoxazol-5-yl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: diisopropylamine / tetrahydrofuran / 0.25 h / -78 °C 1.2: Et3N / tetrahydrofuran / 0.33 h / -78 °C 1.3: 32 percent / tri(2-furyl)phosphine / tris(dibenzylideneacetone)dipalladium; ZnCl2 / 1-methyl-pyrrolidin-2-one; tetrahydrofuran; diethyl ether / 2 h / 20 °C 2.1: 85 percent / AcOH; aq. Bu4NF / tetrahydrofuran / 1.75 h / 0 - 20 °C 3.1: Et3N / CH2Cl2; hexane / 1 h / 20 °C View Scheme |
(5R,6S)-6-[(R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid p-nitrobenzyl ester
(5R,6S)-6-((R)-1-Hydroxy-ethyl)-3-(3-methoxymethyl-isoxazol-5-yl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: diisopropylamine / tetrahydrofuran / 0.5 h / -70 °C 2: Ph3As / ZnCl2, LiCl; tris(dibenzylideneacetone)dipalladium / tetrahydrofuran / 3 h / 20 °C View Scheme |
(5R,6S)-6-[(R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid p-nitrobenzyl ester
p-nitrobenzyl (5R,6S)-6-[(1R)-hydroxyethyl]-2-(1-phenylpyrazol-3-yl)-carbapen-2-em-3-carboxylate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: diisopropylamine / tetrahydrofuran / 0.5 h / -70 °C 2: 67 percent / Ph3As / ZnCl2, LiCl; tris(dibenzylideneacetone)dipalladium / tetrahydrofuran / 3 h / 20 °C View Scheme |
(5R,6S)-6-[(R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid p-nitrobenzyl ester
p-nitrobenzyl (5R,6S)-2-[3-(phenyl)isoxazol-5-yl]-6-[(1R)-1-hydroxyethyl]carbapen-2-em-3-carboxylate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: diisopropylamine / tetrahydrofuran / 0.25 h / -78 °C 1.2: Et3N / tetrahydrofuran / 0.33 h / -78 °C 1.3: 32 percent / tri(2-furyl)phosphine / tris(dibenzylideneacetone)dipalladium; ZnCl2 / 1-methyl-pyrrolidin-2-one; tetrahydrofuran; diethyl ether / 2 h / 20 °C 2.1: 85 percent / AcOH; aq. Bu4NF / tetrahydrofuran / 1.75 h / 0 - 20 °C 3.1: 62 percent / Et3N / CH2Cl2; hexane / 1 h / 20 °C View Scheme |
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