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

Base Information

• Chemical Name: (5R,6S)-4-Nitrobenzyl 6-((R)-1-hydroxyethyl)-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylate
• CAS No.: 74288-40-7
• Molecular Formula: C16H16N2O7
• Molecular Weight: 348.312
• Hs Code.: 2933990090
• European Community (EC) Number: 616-072-7
• UNII: V9J4CAR06A
• DSSTox Substance ID: DTXSID10225303
• Nikkaji Number: J2.536.780D
• Mol file: 74288-40-7.mol

Synonyms:74288-40-7;ADC-13;(5R,6S)-4-Nitrobenzyl 6-((R)-1-hydroxyethyl)-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylate;p-Nitrobenzyl-6-(1-hydroxyethyl)-1-azabicyclo(3.2.0)heptane-3,7-dione-2-carboxylate;p-Nitrobenzyl 6-(1'-Hydroxyethyl)-azabicyclo(3.2.0)heptane-3,7-dione-2-carboxylate;UNII-V9J4CAR06A;V9J4CAR06A;p-Nitrobenzyl (5R,6S)-6-((1R)-1-hydroxyethyl)-2-oxocarbapenam-3-carboxylate;1-Azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-((1R)-1-hydroxyethyl)-3,7-dioxo-, (4-nitrophenyl)methyl ester, (5R,6S)-;(4-nitrophenyl)methyl (5R,6S)-6-[(1R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylate;6-(1-Hydroxy-ethyl)-3,7-dioxo-1-aza-bicyclo(3.2.0)heptane-2-carboxylic Acid 4-Nitro-benzyl Ester;77448-91-0;C16H16N2O7;ADC13;p-Nitrobenzyl 6-(1-hydroxyethyl)-1-azabicyclo[3.2.0]heptane-3,7-dione-2-carboxylate;ADC 13;SCHEMBL3902557;DTXSID10225303;YBIDYTOJOXKBLO-USLOAXSXSA-N;BCP12985;MFCD08458409;AKOS015950836;AKOS040744495;DS-2916;(5R,6S)-4-Nitrobenzyl6-((R)-1-hydroxyethyl)-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylate;AC-15432;Q-101437;Q27291699;4-nitrobenzyl (5R, 6S)-6-[(1R)-1-hydroxyethyl]-2-oxo-1-carbapenam-3-carboxylate;4-nitrobenzyl (5R, 6S)-6-[(1R)-1-hydroxyethyl]-2oxo-1-carbapenam-3-carboxylate;4-nitrobenzyl (5R,6S)-2-oxo-6-((1R)-1-hydroxyethyl) -1-carbapenam-3-carboxylate;4-nitrobenzyl (5R,6S)-6-((1R)-1-hydroxyethyl) -2-oxo-1-carbapenam-3-carboxylate;4-nitrobenzyl (5R,6S)-6-[(1R)-1-hydroxyethyl]-2-oxo-1-carbapenam-3-carboxylate;p-nitrobenzyl (5R, 6S)-6-[(1R)-1-hydroxyethyl]-2-oxo-1-carbapenam-3-carboxylate;p-nitrobenzyl (5R,6S)-6-[(1R)-1-hydroxyethyl]-2-oxo-1-carbapenam-3-carboxylate;(5beta)-6beta-[(R)-1-Hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4-nitrobenzyl ester;(5R, 6S) p-nitrobenzyl 6-[(R)-1-hydroxyethyl]-1-azabicyclo[3.2.0]heptan-3,7-dione-2-carboxylate;(5R,6S) p-nitrobenzyl 6-[(R)-1-hydroxyethyl]-1-azabicyclo[3.2.0]heptan-3,7-dione-2-carboxylate;1-Azabicyclo[3.2.0]heptane-2-carboxylicacid, 6-[(1R)-1-hydroxyethyl]-3,7-dioxo-, (4-nitrophenyl)methyl ester, (5R,6S)-;4-nitrobenzyl (5R,6S)-3,7-dioxo-6-{(1R)-1-hydroxyethyl}-1-azabicyclo[3.2.0]heptane-2-carboxylate;4-Nitrobenzyl (5R,6S)-6-[(1R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylate, Antibiotic for Culture Media Use O nly;6-[(1R)-1-Hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid (5R,6S)-(4-nitrophenyl)methyl ester;p-nitrobenzyl (5R, 6S)-6-[1-(R)-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylate;p-Nitrobenzyl 6-(1 inverted exclamation mark -Hydroxyethyl)-azabicyclo(3.2.0)heptane-3,7-dione-2-carboxylate

Chemical Property of (5R,6S)-4-Nitrobenzyl 6-((R)-1-hydroxyethyl)-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylate

Chemical Property:

• Appearance/Colour: White to off-white powder
• Vapor Pressure: 2.63E-15mmHg at 25°C
• Melting Point: 108-110oC
• Refractive Index: 1.631
• Boiling Point: 607.5 °C at 760 mmHg
• PKA: 11.26±0.40(Predicted)
• Flash Point: 321.2 °C
• PSA: 129.73000
• Density: 1.56 g/cm³
• LogP: 0.64830
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 5
• Exact Mass: 348.09575085
• Heavy Atom Count: 25
• Complexity: 594

Purity/Quality:

98.5% ^*data from raw suppliers

CKB ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C1C2CC(=O)C(N2C1=O)C(=O)OCC3=CC=C(C=C3)[N+](=O)[O-])O
• Isomeric SMILES: C[C@H]([C@@H]1[C@H]2CC(=O)C(N2C1=O)C(=O)OCC3=CC=C(C=C3)[N+](=O)[O-])O
• Uses: Imipenem intermediate.

Technology Process of (5R,6S)-4-Nitrobenzyl 6-((R)-1-hydroxyethyl)-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylate

There total 32 articles about (5R,6S)-4-Nitrobenzyl 6-((R)-1-hydroxyethyl)-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

(3RS,4RS)-α-diazo-3-[1(RS)-hydroxyethyl]-β,2-dioxo-4-azetidinebutanoic acid p-nitrobenzyl ester → p-nitrobenzyl 6-(1'-hydroxyethyl)-1-azabicyclo(3.2.0)heptane-3,7-dione-2-carboxylate (74288-40-7,75363-99-4,77171-48-3,77448-91-0,77449-43-5,78184-67-5,111468-09-8,115938-32-4)

Guidance literature:

dirhodium tetraacetate; zinc dibromide; In ethyl acetate; at 75 - 77 ℃; for 1h; Product distribution / selectivity;

Reference yield:

(3S,4R)-3-[(R)-1-hydroxyethyl)-4-[3-(4-nitrobenzyl)oxycarbonyl-2-oxo-3-diazopropyl]azetidin-2-one (74288-39-4) → (5R,6S)-6-[(R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid p-nitrobenzyl ester (74288-40-7)

Guidance literature:

With dirhodium tetraacetate; In toluene; at 80 ℃; for 2.5h;

DOI:10.1016/S0960-894X(00)00248-1

Reference yield:

(3S,4R)-3-[(R)-1-hydroxyethyl]-4-[3-(4-nitrobenzyl)oxycarbonyl-2-oxo-3-diazopropyl]azetidin-2one → (5R,6S)-6-[(R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid p-nitrobenzyl ester (74288-40-7)

Guidance literature:

With nitrogen; rhodium(II) acetate; In benzene;

upstream raw materials:

magnesium 4-nitrobenzyl malonate

[(2S,3R)-3-(1-Hydroxy-ethyl)-4-oxo-azetidin-2-yl]-acetic acid

4-[(2S,3R)-3-(1-Hydroxy-ethyl)-4-oxo-azetidin-2-yl]-3-oxo-butyric acid 4-nitro-benzyl ester

(E)-2-Acetyl-3-benzylamino-pent-2-enedioic acid diethyl ester

Downstream raw materials:

p-nitrobenzyl (6S)-<(1R)-hydroxyethyl>-2--(5R)-carbapen-2-em-3-carboxylate

(5R,6S)-6-(1-Hydroxy-ethyl)-3-[2-(4-nitro-benzyloxycarbonylamino)-ethylsulfanyl]-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

(5R,6S)-6-((R)-1-Hydroxy-ethyl)-3-[2-(4-nitro-benzyloxycarbonylamino)-ethylsulfanyl]-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

p-nitrobenzyl (5R,6S)-3-<(E)-2-acetamidoethylthio>-6-<(R)-1-hydroxyethyl>-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate

Refernces

• 1、 Bodner, Micah J.,Phelan, Ryan M.,Townsend, Craig A.. "A catalytic asymmetric route to carbapenems". scheme or table. p. 3606 - 3609. Retrieved 2011/03/17.
• 2、 Pfaendler, Hans Rudolf,Weishaupt, Ralf,Meffert, Helmut. "Synthesis and biological activities of an α-methyl and a β-methyl carbapenem and the corresponding unsubstituted compound". . p. 1389 - 1391. Retrieved 2007/10/03.