74288-39-4

Basic information

• Product Name: 2-Azetidinebutanoic acid, a-diazo-3-(1-hydroxyethyl)-b,4-dioxo-, (4-nitrophenyl)methyl ester, [2R-[2a,3b(R*)]]-
• CAS NO: 74288-39-4
• Molecular Formula: C16H16N4O7
• Molecular Weight: 376.326
• Mol File: 74288-39-4.mol
• Article Data: 17

Chemical Properties

• CAS DataBase Reference: 2-Azetidinebutanoic acid, a-diazo-3-(1-hydroxyethyl)-b,4-dioxo-, (4-nitrophenyl)methyl ester, [2R-[2a,3b(R*)]]-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Azetidinebutanoic acid, a-diazo-3-(1-hydroxyethyl)-b,4-dioxo-, (4-nitrophenyl)methyl ester, [2R-[2a,3b(R*)]]-(74288-39-4)
• EPA Substance Registry System: 2-Azetidinebutanoic acid, a-diazo-3-(1-hydroxyethyl)-b,4-dioxo-, (4-nitrophenyl)methyl ester, [2R-[2a,3b(R*)]]-(74288-39-4)

Safety Data

• Hazardous Substances Data: 74288-39-4(Hazardous Substances Data)

Usage

Type of compound

Diazoketone derivative

Use

Organic synthesis, preparation of peptides and other organic compounds

Properties

Ability to introduce the diazo group into organic molecules

Safety

Handle with care, potentially explosive if not handled properly

Upstream product

• 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 
• 115936-64-6 (3S,4R)-3-<(R)-1'-(dimethyl-t-butylsilyloxy)ethyl>-4-oxoazetidin-2-carboxylic acid 
• 1180012-50-3 (3S,4R)-benzyl 3-((R)-1-(tert-butyldimethylsilyloxy)ethyl)-azetidin-2-one-4-carboxylate 
• 1180012-46-7 (3S,4R)-benzyl N-(p-toluenesulfonyl)-3-((R)-1-(tert-butyldimethylsilyloxy)ethyl)-azetidin-2-one-4-carboxylate 
• 17202-49-2 p-carboxybenzenesulfonyl azide 
• 79791-38-1 4-dodecylbenzenesulphonyl azide 
• 84362-42-5 <3S-<3α(S^*),4β>>-3-(1-t-butyldimethylsilyloxyethyl)-4-iodomethyl-2-azetidinone 
• 86279-95-0 (E)-4-{(2R,3S)-1-(tert-Butyl-dimethyl-silanyl)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-but-2-enoic acid 4-nitro-benzyl ester 
• 86279-90-5 (3S,4R)-1-(tert-Butyl-dimethyl-silanyl)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-[2-(4,5-dihydro-thiazol-2-ylsulfanyl)-but-3-enyl]-azetidin-2-one 
• 86279-93-8 (E)-4-{(2R,3S)-1-(tert-Butyl-dimethyl-silanyl)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-but-2-enoic acid 
• 86279-88-1 (E)-4-[(2R,3S)-3-((R)-1-Hydroxy-ethyl)-4-oxo-azetidin-2-yl]-but-2-enoic acid 4-nitro-benzyl ester 
• 90024-54-7 (E)-4-{(2R,3S)-1-(tert-Butyl-dimethyl-silanyl)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-but-2-enal 
• 86279-91-6 (3S,4R)-1-(tert-Butyl-dimethyl-silanyl)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-((E)-4-iodo-but-2-enyl)-azetidin-2-one 

Downstream Products

• 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 
• 80951-83-3 p-nitrobenzyl (5R,6S)-3-<(E)-2-acetamidoethylthio>-6-<(R)-1-hydroxyethyl>-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate 
• 74288-40-7 (5R,6S)-6-[(R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid p-nitrobenzyl ester 
• 59995-64-1 thienamycin 
• 75363-99-4 4-nitrobenzyl (2R,5R,6S)-6-[(1R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylate 

Relevant articles and documents

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Stereoselective reactions. XX. Synthetic studies on optically active β-lactams. III. Stereocontrolled synthesis of chiral intermediate to (+)-thienamycin from D-glucose

A chiral key intermediate (19a) for the synthesis of (+)-thienamycin was synthesized starting from D-glucose. The enol ether 13, obtained from the ketone 11 by Horner-Wittig reaction, was transformed to the corresponding methyl ester 16 by pyridinium chlorochromate oxidation or by employing the Wacker process. The ester 16 was further converted to the β-lactam 19a, which is a useful chiral precursor to (+)-thienamycin.