75321-07-2

Basic information

• Product Name: (3S,4R)-3-[(R)-1-hydroxyethyl]-4-[3-(4-nitrobenzyl)-oxycarbonyl-2-oxopropyl]azetidin-2-one
• Synonyms: (3S,4R)-3-[(R)-1-hydroxyethyl]-4-[3-(4-nitrobenzyl)-oxycarbonyl-2-oxopropyl]azetidin-2-one
• CAS NO: 75321-07-2
• Molecular Weight: 350.328
• Mol File: 75321-07-2.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: (3S,4R)-3-[(R)-1-hydroxyethyl]-4-[3-(4-nitrobenzyl)-oxycarbonyl-2-oxopropyl]azetidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,4R)-3-[(R)-1-hydroxyethyl]-4-[3-(4-nitrobenzyl)-oxycarbonyl-2-oxopropyl]azetidin-2-one(75321-07-2)
• EPA Substance Registry System: (3S,4R)-3-[(R)-1-hydroxyethyl]-4-[3-(4-nitrobenzyl)-oxycarbonyl-2-oxopropyl]azetidin-2-one(75321-07-2)

Safety Data

• Hazardous Substances Data: 75321-07-2(Hazardous Substances Data)

Upstream product

• 18933-62-5 methyl 3-azido-4-O-benzoyl-6-bromo-2,3,6-trideoxy-α-D-arabino-hexopyranoside 
• 78477-86-8 (3S,4R)-3-<(R)-1-hydroxyethyl>-4-<(benzyloxycarbonyl)methyl>-2-azetidinone 
• 105995-50-4 magnesium 4-nitrobenzyl malonate 
• 78501-85-6 [(2S,3R)-3-(1-Hydroxy-ethyl)-4-oxo-azetidin-2-yl]-acetic acid 
• 78963-47-0 rac-3-{1-[(tert-Butyldimethylsilyl)oxy]ethyl}-4-acetoxyazetidin-2-one 
• 77359-11-6 propanedioic acid mono[(4-nitrophenyl)methyl] ester 
• 75321-06-1 (3S,4R)-1-(t-butyldimethylsilyl)-3-[(R)-1-hydroxyethyl]-4-(3-p-nitrobenzyloxycarbonyl-2-oxopropyl)-azetidin-2-one 
• 78501-85-6 [(2R,3S)-3-((R)-1-Hydroxy-ethyl)-4-oxo-azetidin-2-yl]-acetic acid 
• 77120-95-7 (2S,3R)-3-Amino-2-((S)-1-hydroxy-ethyl)-pentanedioic acid 5-benzyl ester; hydrochloride 
• 77120-97-9 {(2R,3S)-1-(tert-Butyl-dimethyl-silanyl)-3-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-acetic acid benzyl ester 
• 77120-94-6 t-4-amino-c-2-methyl-6-oxotetrahydropyran-r-3-carboxylic acid hydrochloride 
• 77120-98-0 {(2R,3S)-1-(tert-Butyl-dimethyl-silanyl)-3-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-acetic acid 
• 77120-96-8 benzyl -4-oxoazetidin-2-yl> acetate 
• 77120-92-4 (2R,3S)-3-Benzylamino-2-((R)-1-hydroxy-ethyl)-pentanedioic acid diethyl ester 

Downstream Products

• 75363-99-4 4-nitrobenzyl (2R,5R,6S)-6-[(1R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylate 
• 64067-13-6 p-nitrobenzyl (5R,6S)-2-<<2-<<<(p-nitrobenzyl)oxy>carbonyl>amino>ethyl>thio>-6-<(R)-1-hydroxyethyl>carbapen-2-em-3-carboxylate 
• 75321-08-3 p-nitrobenzyl (5R,6S)-2-diphenoxy phosphoryloxy-6-[(R)-1-hydroxyethyl]-1-carbapen-2-em-3-carboxylate 
• 64067-13-6 (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 
• 74288-40-7 (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 
• 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 
• 75321-07-2 4-[(2S,3R)-3-((S)-1-Hydroxy-ethyl)-4-oxo-azetidin-2-yl]-3-oxo-butyric 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 
• 59995-64-1 thienamycin 
• 74288-40-7 (2S,5S,6R)-6-((R)-1-Hydroxy-ethyl)-3,7-dioxo-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl ester 
• 79543-87-6 4-[(2S,3R)-3-((S)-1-Formyloxy-ethyl)-4-oxo-azetidin-2-yl]-3-oxo-butyric acid 4-nitro-benzyl ester 

Relevant articles and documents

β-Lactams. 2. Diastereoselective Alkylative Discrimination of Racemic 3-Substituted 4-Acetoxyazetidin-2-ones and Its Application to the Synthesis of a Chiral Key Intermediate for Carbapenem Syntheses

Alkylation of rac 3-substituted 4-acetoxyazetidin-2-one 4 with chiral tin(II) enolate 8 derived from 3-acetyl-(4S)-ethyl-1,3-thiazolidine-2-thione (ETT) (7) proceeded in a highly diastereoselective manner to give alkylated products 9, 10, and 11 in 42percent, 20percent, and 9percent yields, respectively, after chromatographic purification.Similar alkylation of rac-5 with 8 gave 16, 17, and 18 in 45percent, 29percent, and 5percent yields, respectively.Compound 9 was readily converted to 33, a chiral key intermediate for the synthesis of carbapenems.Analytical separation of rac-4 was effectively done with an HPLC technique employing a chiral column packed with A(S)MBC.

Simple and Condensed β-Lactams. Part 9. Elaboration of the 3-(1-Hydroxyethyl) Side Chains of Potential Intermediates of Carbapenem Antibiotics via the 2-Methyl-1,3-dioxolan-2-yl Group

Deketalization of the trans compounds methyl and ethyl (2RS,3RS)-1-(2,4-dimethoxybenzyl)-3-(2-methyl-1,3-dioxolan-2-yl)-4-oxoazetidine-2-carboxylates 5b and 5c, and of the cis isomer (6b) of the latter leads to 85:15 mixtures of the trans- and cis-compounds methyl (2RS,3RS)- and (2RS,3SR)-3-acetyl-1-(2,4-dimethoxybenzyl)-4-oxoazetidine-2-carboxylate (7a) and (8a), respectively of the corresponding ethyl esters (7b) and (8b).Sodium borohydride reduction of the mixture of the trans- and cis-esters (7b) and (8b) gives a mixture of the 1'-epimeric trans-compounds ethyl(2RS,3RS)-1-(2,4-dimethoxybenzyl)-3--4-oxazetidine-2-carboxylate (9b) and (10b).Similar mixtures of 1'-epimeric compounds of the types (9) and (10), carrying a variety of substituents attached to position 2 of their azetidine rings were obtained by successive deketalization and reduction of the corresponding trans-(5) and cis-(6) compounds or their mixtures, as well as by other methods.Ring closure of a mixture of the pair of the 1'-epimeric trans-compounds p-nitrobenzyl 2-diazo-4--4-oxo-azetidin-2-yl>-3-oxobutanoates (9n) and (10n) gave a mixture of the 1'-epimeric compounds p-nitrobenzyl 6--2,7-dioxo-(3RS,5RS,6SR)-carbapenam-3-carboxylates (11) and (12) which was converted into a mixture (13) of the 1'-epimeric bis-protected thienamycin analogues p-nitrobenzyl 2-(2-formylaminoethylthio)-6--7-oxo-(5RS,6SR)-carbapen-2-em-3-carboxylates.

FROM PENICILLIN TO PENEM AND CARBAPENEM. SYNTHESIS OF 2-OXOCARBAPENAM DERIVATIVE

Previously obtained 4-iodomethylazetidinone derivative (2a) is transformed via the trans-iodopropenylation method into the β-keto ester (8), which is thought to be an important precursor for the synthesis of the carbapenem derivatives.