p-Nitrobenzyl (5R,6S)-2-(diphenylphosphoryloxy)-6-((1R)-1-hydroxyethyl)carbapen-2-em-3-carboxylate

Base Information

• Chemical Name: p-Nitrobenzyl (5R,6S)-2-(diphenylphosphoryloxy)-6-((1R)-1-hydroxyethyl)carbapen-2-em-3-carboxylate
• CAS No.: 75321-08-3
• Molecular Formula: C28H25N2O10P
• Molecular Weight: 580.488
• UNII: FJ9K0JDB31
• DSSTox Substance ID: DTXSID60226284
• Wikidata: Q27278018
• Mol file: 75321-08-3.mol

Synonyms:75321-08-3;p-Nitrobenzyl (5R,6S)-2-(diphenylphosphoryloxy)-6-((1R)-1-hydroxyethyl)carbapen-2-em-3-carboxylate;UNII-FJ9K0JDB31;FJ9K0JDB31;(4-nitrophenyl)methyl (5R,6S)-3-diphenoxyphosphoryloxy-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate;1-Azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid, 3-((diphenoxyphosphinyl)oxy)-6-((1R)-1-hydroxyethyl)-7-oxo-, (4-nitrophenyl)methyl ester, (5R,6S)-;DTXSID60226284;VVLXPESSYNCTFQ-DVKBMCPXSA-N;(4-nitrophenyl)methyl (5R,6S)-3-[(diphenoxyphosphoryl)oxy]-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate;4-nitrobenzyl (5R,6S)-3-((diphenoxyphosphoryl)oxy)-6-((R)-1-hydroxyethyl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate;AKOS015964877;AC-4678;Q27278018;(5R,6S)-3-(Diphenoxy-phosphoryloxy)-6-(1-hydroxy-ethyl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester;(5R,6S)-4-nitrobenzyl 3-(diphenoxyphosphoryloxy)-6-((R)-1-hydroxyethyl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate;p-nitrobenzyl (5R,6S)-2-diphenoxyphosphoryloxy-6-[(R)-1-hydroxyethyl]-1-carbapen-2-em-3-carboxylate

Chemical Property of p-Nitrobenzyl (5R,6S)-2-(diphenylphosphoryloxy)-6-((1R)-1-hydroxyethyl)carbapen-2-em-3-carboxylate

Chemical Property:

• Vapor Pressure: 7.87E-22mmHg at 25°C
• Refractive Index: 1.661
• Boiling Point: 721.2 °C at 760 mmHg
• PKA: 14.36±0.20(Predicted)
• Flash Point: 390 °C
• PSA: 167.23000
• Density: 1.49 g/cm³
• LogP: 5.20490
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 11
• Exact Mass: 580.12468200
• Heavy Atom Count: 41
• Complexity: 1030

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C1C2CC(=C(N2C1=O)C(=O)OCC3=CC=C(C=C3)[N+](=O)[O-])OP(=O)(OC4=CC=CC=C4)OC5=CC=CC=C5)O
• Isomeric SMILES: C[C@H]([C@@H]1[C@H]2CC(=C(N2C1=O)C(=O)OCC3=CC=C(C=C3)[N+](=O)[O-])OP(=O)(OC4=CC=CC=C4)OC5=CC=CC=C5)O
• Uses: p-Nitrobenzyl(5R,6S)-2-(diphenylphosphoryloxy)-6-((1R)-1-hydroxyethyl)carbapen-2-em-3-carboxylate is a useful intermediate in the preparation of novel dithiocarbamate carbapenems with anti-?MRSA activity.

Technology Process of p-Nitrobenzyl (5R,6S)-2-(diphenylphosphoryloxy)-6-((1R)-1-hydroxyethyl)carbapen-2-em-3-carboxylate

There total 45 articles about p-Nitrobenzyl (5R,6S)-2-(diphenylphosphoryloxy)-6-((1R)-1-hydroxyethyl)carbapen-2-em-3-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:

4-nitrobenzyl (2R,5R,6S)-6-[(1R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylate (75363-99-4) + chlorophosphoric acid diphenyl ester (2524-64-3) → p-nitrobenzyl (5R,6S)-2-diphenoxy phosphoryloxy-6-[(R)-1-hydroxyethyl]-1-carbapen-2-em-3-carboxylate (75321-08-3)

Guidance literature:

With dmap; N-ethyl-N,N-diisopropylamine; In acetonitrile; at 0 ℃;

DOI:10.1021/ja00539a040

Reference yield:

(3S,4R)-3-[(R)-1-hydroxyethyl]-4-[3-(4-nitrobenzyl)-oxycarbonyl-2-oxopropyl]azetidin-2-one (75321-07-2) → p-nitrobenzyl (5R,6S)-2-diphenoxy phosphoryloxy-6-[(R)-1-hydroxyethyl]-1-carbapen-2-em-3-carboxylate (75321-08-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 74 percent / p-carboxybenzenesulfonyl azide, TEA / ethyl acetate / 0.5 h / Ambient temperature

2: 74 percent / Rh₂(OAc)4 / benzene / 0.05 h / Heating

3: N,N-diisopropylethylamine / acetonitrile / 1.5 h / -20 °C

With TEA; p-carboxybenzenesulfonyl azide; N-ethyl-N,N-diisopropylamine; dirhodium tetraacetate; In ethyl acetate; acetonitrile; benzene;

DOI:10.1248/cpb.39.2201

Reference yield:

(3S,4R)-3-[(R)-1-hydroxyethyl)-4-[3-(4-nitrobenzyl)oxycarbonyl-2-oxo-3-diazopropyl]azetidin-2-one (74288-39-4) → p-nitrobenzyl (5R,6S)-2-diphenoxy phosphoryloxy-6-[(R)-1-hydroxyethyl]-1-carbapen-2-em-3-carboxylate (75321-08-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 74 percent / Rh₂(OAc)4 / benzene / 0.05 h / Heating

2: N,N-diisopropylethylamine / acetonitrile / 1.5 h / -20 °C

With N-ethyl-N,N-diisopropylamine; dirhodium tetraacetate; In acetonitrile; benzene;

DOI:10.1248/cpb.39.2201

upstream raw materials:

(5R,6S)-6-(1-Hydroxy-ethyl)-3,7-dioxo-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl ester

chlorophosphoric acid diphenyl ester

p-nitrobenzyl 6-(1'-hydroxyethyl)-1-azabicyclo(3.2.0)heptane-3,7-dione-2-carboxylate

(2S,5S,6R)-6-((S)-1-Hydroxy-ethyl)-3,7-dioxo-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl ester

Downstream raw materials:

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

N-formimidoyl thienamycin

thienamycin

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

Refernces

• 1、 Ishikawa, Katsuya,Kojima, Katsuhiko,Miyauchi, Masao,Endo, Rokuro,Yasuda, Hiroshi,Kawamoto, Isao. "Synthesis and structure-activity relationships of 1β-methylcarbapenems with quaternary ammonium side chains". . p. 757 - 770. Retrieved 2007/10/03.
• 2、 Shinkai, I.,Reamer, R. A.,Hartner, F. W.,Liu, T.,Sletzinger, M.. "A DIRECT TRANSFORMATION OF BICYCLIC KETO ESTERS TO N-FORMIMIDOYL THIENAMYCIN". . p. 4903 - 4906. Retrieved 2007/10/02.