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

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

• 93861-39-3 (3S,4R)-3-[(1R)-(tert-butyldimethyl-silyloxy)ethyl]-4-[3-(4-nitrobenzyloxy)carbonyl-2-oxo-3-diazopropyl]azetidin-2-one 
• 84016-91-1 tetrahydro-2β-methyl-6-oxo-4β-amino-2H-pyran-3α-carboxylic acid hydrochloride 
• 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 
• 75321-07-2 (3S,4R)-3-[(R)-1-hydroxyethyl]-4-[3-(4-nitrobenzyl)-oxycarbonyl-2-oxopropyl]azetidin-2-one 
• 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 

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

Atypical Carbapenem Antibiotics with Improved Activity Against Carbapenemase-Producing Acinetobacter baumannii

The following invention deals with the design, preparation, evaluation, and use of carbapenem antibiotics with improved activity, relative to current commercially available carbapenem antibiotics, against infections involving multidrug resistant, carbapen

A catalytic asymmetric route to carbapenems

Image Presented Efficient syntheses of N-acetyl thienamycin and epithienamycin A in their readily deprotected form are reported where three contiguous stereocenters are established in a single catalytic asymmetric azetidinone-forming reaction. These examples are a template for synthesizing C-5/C-6 cis or trans carbapenems with independent control of the C-8 stereocenter. A library of oxidatively and sterochemically defined azetidinone precursors to a variety of naturally occurring carbapenems and potential biosynthetic intermediates has been prepared to facilitate studies of carbapenem antibiotic biosynthesis.

Efficient method for silylation of p-nitrobenzyl-2-diazoacetoacetate

An efficient new method for the silylation of p-nitrobenzyl-2- diazoacetoacetate using hexamethyl disilane and iodine is presented. Copyright Taylor & Francis LLC.

PROCESS FOR PREPARATION OF ESTERS OF 2-DIAZO-3-TRIMETHYLSILYLOXY-3-BUTENOIC ACID

The present invention relates to a process for the preparation of esters of 2-diazo-3-trimethylsilyloxy-3-butenoic acid which comprises reacting a diazoacetoacetate with iodotrimethylsilane in the presence of an organic base, wherein iodotrimethylsilane is prepared by reacting hexamethyldisilane with iodine. The present invention further relates to converting such esters of 2-diazo-3-trimethylsilyloxy-3-butenoic acid to other compounds, such as a substituted diazoazetidinone, an azetidinone, or a bicyclo ketoester.

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

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Carbapenem intermediates

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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.

3-[1-Hydroxyethyl]-4-carboxymethyl-azetidin-2-one

In a process for the total synthesis of thienamycin from L-aspartic acid via intermediate III: STR1 there is disclosed a process for preparing III via STR2 wherein R is a protecting group.