64067-13-6

Basic information

• Product Name: (4-nitrophenyl)methyl [5R-[5alpha,6alpha(R*)]]-6-(1-hydroxyethyl)-3-[[2-[[[(4-nitrophenyl)methoxy]carbonyl]amino]ethyl]thio]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
• Synonyms: (4-nitrophenyl)methyl [5R-[5alpha,6alpha(R*)]]-6-(1-hydroxyethyl)-3-[[2-[[[(4-nitrophenyl)methoxy]carbonyl]amino]ethyl]thio]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate;(5R)-6β-[(R)-1-Hydroxyethyl]-3-[[2-[[[(4-nitrophenyl)methoxy]carbonyl]amino]ethyl]thio]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (4-nitrophenyl)methyl ester
• CAS NO: 64067-13-6
• Molecular Formula: C₂₆H₂₆N₄O₁₀S
• Molecular Weight: 586.57044
• EINECS: 264-650-9
• Mol File: 64067-13-6.mol
• Article Data: 11

Chemical Properties

• Melting Point: 184-185 °C
• Boiling Point: 840.2±65.0 °C(Predicted)
• Appearance: /
• Density: 1.52±0.1 g/cm3(Predicted)
• PKA: 11.72±0.46(Predicted)
• CAS DataBase Reference: (4-nitrophenyl)methyl [5R-[5alpha,6alpha(R*)]]-6-(1-hydroxyethyl)-3-[[2-[[[(4-nitrophenyl)methoxy]carbonyl]amino]ethyl]thio]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: (4-nitrophenyl)methyl [5R-[5alpha,6alpha(R*)]]-6-(1-hydroxyethyl)-3-[[2-[[[(4-nitrophenyl)methoxy]carbonyl]amino]ethyl]thio]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate(64067-13-6)
• EPA Substance Registry System: (4-nitrophenyl)methyl [5R-[5alpha,6alpha(R*)]]-6-(1-hydroxyethyl)-3-[[2-[[[(4-nitrophenyl)methoxy]carbonyl]amino]ethyl]thio]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate(64067-13-6)

Safety Data

• Hazardous Substances Data: 64067-13-6(Hazardous Substances Data)

Usage

Uses

(5R,6S)-6-[(1R)-1-Hydroxyethyl]-3-[[2-[[[(4-nitrophenyl)methoxy]carbonyl]amino]ethyl]thio]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic Acid (4-Nitrophenyl)methyl Ester is an intermediate in the synthesis of Thienamycin (T344270). Thienamycin is one of the most potent naturally produced antibiotics known thus far. It has excellent activity against both Gram-positive and Gram-negative bacteria and is resistant to bacterial β-lactamase enzymes.

Upstream product

• 1027190-26-6 4-[(2R,3S)-3-((R)-1-Hydroxy-ethyl)-4-oxo-azetidin-2-yl]-3-[2-(4-nitro-benzyloxycarbonylamino)-ethylsulfanyl]-2-oxo-butyric acid 4-nitro-benzyl ester 
• 65750-59-6 2-(4-nitrobenzyloxycarbonylamino)ethanethiol 
• 18933-62-5 methyl 3-azido-4-O-benzoyl-6-bromo-2,3,6-trideoxy-α-D-arabino-hexopyranoside 
• 75321-08-3 (5R,6S)-3-(Diphenoxy-phosphoryloxy)-6-((R)-1-hydroxy-ethyl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester 
• 75321-08-3 (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 
• 77396-81-7 (5R,6S)-6-(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 
• 135439-84-8 (5R,6S)-6-(1-Hydroxy-ethyl)-7-oxo-3-trifluoromethanesulfonyloxy-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester 
• 77396-88-4 (5R,6S)-3-(Diethoxy-phosphoryloxy)-6-(1-hydroxy-ethyl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester 
• 74288-39-4 (3S,4R)-3-[(R)-1-hydroxyethyl)-4-[3-(4-nitrobenzyl)oxycarbonyl-2-oxo-3-diazopropyl]azetidin-2-one 
• 84016-91-1 tetrahydro-2β-methyl-6-oxo-4β-amino-2H-pyran-3α-carboxylic acid hydrochloride 
• 75321-07-2 (3S,4R)-3-[(R)-1-hydroxyethyl]-4-[3-(4-nitrobenzyl)-oxycarbonyl-2-oxopropyl]azetidin-2-one 
• 78477-86-8 (3S,4R)-3-<(R)-1-hydroxyethyl>-4-<(benzyloxycarbonyl)methyl>-2-azetidinone 
• 67693-33-8 methyl-3-amino-2,3,6-tridesoxy-α-D-arabino-hexopyranoside 
• 74299-77-7 (3S,4R)-1-(tert-butyldimethylsilyl)-3-[(1R)-1-tert-butyldimethylsilyloxyethyl]-4-(2-oxoethyl)-2-azetidinone 

Downstream Products

• 67245-90-3 bis (p-nitrobenzyloxycarbonylaminoethyl)disulfide 
• 77126-89-7 3-Hydroxy-5-((1S,2R)-2-hydroxy-1-methoxycarbonyl-propyl)-1H-pyrrole-2-carboxylic acid 4-nitro-benzyl ester 
• 72778-08-6 p-nitrobenzyl (3S,5S,6S)-2-<<2-<<<(p-nitrobenzyl)oxy>carbonyl>amino>ethyl>thio>-6-<(R)-1-hydroxyethyl>carbapen-1-em-3-carboxylate 
• 59995-64-1 thienamycin 
• 71310-87-7 p-nitrobenzyl (5R,6S)-6-<(R)-1-hydroxyethyl>-2-(<2-((<(p-nitrobenzyl)oxy>carbonyl)amino)ethyl>sulfonyl)carbapen-2-em-3-carboxylate 
• 72843-08-4 (2S,5S,6S)-3-[2-(4-Nitro-benzyloxycarbonylamino)-ethylsulfanyl]-6-[(R)-1-(4-nitro-benzyloxycarbonyloxy)-ethyl]-7-oxo-1-aza-bicyclo[3.2.0]hept-3-ene-2-carboxylic acid 4-nitro-benzyl ester 
• 77171-32-5 Δ¹-thienamycin 
• 96246-72-9 p-nitrobenzyl (5R,6S)-6-<(R)-1-hydroxyethyl>-2-<<2-(methylsulfonyl)ethyl>(<(p-nitrobenzyl)oxy>carbonyl)-amino>carbapen-2-em-3-carboxylate 
• 72778-09-7 N-<<(p-nitrobenzyl)oxy>carbonyl>-O-<<(p-nitrobenzyl)oxy>carbonyl>thienamycin p-nitrobenzyl ester 

Relevant articles and documents

A new strategy for the synthesis of carbapenems. A formal total synthesis of (+)-thienamycin

A new approach to formation of the carbapenem ring system is presented. The key step involves the Lewis acid mediated cyclocondensation of a β-lactam nitrogen and the α-keto ester of a suitably disposed side-chain. The preparation of a known and pivotal intermediadate in the synthesis of thienamycin serves to demonstrate this strategy.

A Novel Ring-Closure Strategy for the Carbapenems: The Total Synthesis of (+)-Thienamycin

Intramolecular Michael cyclization of an N--4-(3-nitro-2-propenyl)-3-oxoazetidin-2-one available in optically pure form leads to the corresponding carbapenam skeleton.Further elaboration via oxidative cleavage of an exocyclic nitromethylene group gives an advanced intermediate, which was transformed into (+)-thienamycin.The stereochemistry of the Michael cyclization and the pitfalls of protective group chemistry are discussed.

Inversion of Configuration at C-8 in the Olivanic Acids: Conversion into the Thienamycins and Other Novel Derivatives

The inversion of stereochemistry at C-8 in the olivanic acids, MM 22383 (7) and MM 22381 (6), is described.The reaction of p-nitrobenzyl (5R,6S)-3--6--7-oxo-1-azabicyclohept-2-ene-2-carboxylate (8) with diethyl azodicarboxylate, triphenylphosphine, and formic acid afforded the 6- derivative (17), which upon alkaline hydrolysis gave the 6- derivative (18).Hydrolysis of the p-nitrobenzyl ester (18) furnished the sodium salt of N-acetyldehydrothienamycin (15), the (8R)-epimer of the olivanic acid MM 22383 (7).The 3-(2-acetamidoethylthio)-analogue, MM 22381 (6), was converted into N-acetylthienamycin (14) by performing a similar series of reactions on its p-nitrobenzyl ester (10).The transformation of the ester (18) to bis-protected thienamycin (22), via the C-3 thiol (21), is also described.Reaction of the olivanic acid esters (8) and (10) with diethyl azodicarboxylate, triphenylphosphine and hydrazoic acid resulted in the formation of the 6- derivatives (27) and (28).Subsequent hydrolysis provided (5R,6R)-3--6--7-oxo-1-azabicyclohept-2-ene-2-carboxylic acid (29) and the 3-(2-acetamidoethylthio)-analogue (30).