75321-08-3

Usage

Uses

Used in Pharmaceutical Industry:
(5R,6S)-3-[(Diphenoxyphosphinyl)oxy]-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (4-nitrophenyl)methyl ester is used as an intermediate in the synthesis of novel dithiocarbamate carbapenems. These carbapenems possess potent anti-MRSA (Methicillin-resistant Staphylococcus aureus) activity, making them valuable in the development of new antibiotics to combat drug-resistant bacterial infections.
Used in Chemical Research:
(5R,6S)-3-[(Diphenoxyphosphinyl)oxy]-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (4-nitrophenyl)methyl ester can also be utilized in chemical research as a starting material or a building block for the synthesis of other complex organic molecules. Its unique structure and functional groups make it a promising candidate for further exploration and development in various chemical applications.

InChI:InChI=1/C28H25N2O10P/c1-18(31)25-23-16-24(40-41(36,38-21-8-4-2-5-9-21)39-22-10-6-3-7-11-22)26(29(23)27(25)32)28(33)37-17-19-12-14-20(15-13-19)30(34)35/h2-15,18,23,25,31H,16-17H2,1H3/t18-,23-,25-/m1/s1

Upstream product

• 74288-40-7 (5R,6S)-6-(1-Hydroxy-ethyl)-3,7-dioxo-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl ester 
• 2524-64-3 chlorophosphoric acid diphenyl ester 
• 74288-40-7 p-nitrobenzyl 6-(1'-hydroxyethyl)-1-azabicyclo(3.2.0)heptane-3,7-dione-2-carboxylate 
• 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 
• 77120-91-3 (E)-2-Acetyl-3-benzylamino-pent-2-enedioic acid diethyl ester 
• 77120-92-4 (2R,3S)-3-Benzylamino-2-((R)-1-hydroxy-ethyl)-pentanedioic acid diethyl 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 
• 77120-96-8 benzyl -4-oxoazetidin-2-yl> acetate 
• 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 
• 75321-07-2 4-[(2S,3R)-3-((S)-1-Hydroxy-ethyl)-4-oxo-azetidin-2-yl]-3-oxo-butyric acid 4-nitro-benzyl ester 
• 75321-07-2 4-[(2S,3R)-3-((R)-1-Hydroxy-ethyl)-4-oxo-azetidin-2-yl]-3-oxo-butyric acid 4-nitro-benzyl ester 
• 77120-94-6 t-4-amino-c-2-methyl-6-oxotetrahydropyran-r-3-carboxylic acid 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 
• 77120-95-7 (2S,3R)-3-Amino-2-((S)-1-hydroxy-ethyl)-pentanedioic acid 5-benzyl ester; hydrochloride 

Downstream Products

• 85737-71-9 C₂₂H₃₀N₄O₆SSi 
• 64221-86-9 N-formimidoyl thienamycin 
• 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 
• 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 
• 59995-64-1 thienamycin 
• 192884-04-1 (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 
• 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 
• 64067-13-6 (5R,6S)-6-(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 

Relevant academic research and scientific papers

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.

Synthesis and structure-activity relationships of 1β-methylcarbapenems with quaternary ammonium side chains

The synthesis and antibacterial activity of 1β-methylcarbapenems with quaternary ammonium groups at the C-2 position have been studied. Two types of new carbapenem derivatives have been synthesized. These 1β-methylcarbapenems, one type having a (2S,4S)-2-[1,1-dimethyl-2-(1-piperazinyl)carbonyl]pyrrolidinio-4-ylthio group and the other type having a (2S,4S)-2-(4-carbamoylmethyl-4-methylhomopiperazinio-1-ylcarbon-yl)pyrrolidin-4 -ylthio group, show potent and well balanced antibacterial activity as well as high stability against dehydropeptidase-I. The in vivo potency of these two carbapenems was compared with that of meropenem. The structure-activity relationships leading to these carbapenems are also described.

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.

A DIRECT TRANSFORMATION OF BICYCLIC KETO ESTERS TO N-FORMIMIDOYL THIENAMYCIN

A convenient direct transformation of p-nitrobenzyl 6-(1'-hydroxyethyl)-azabicyclo-(3.2.0)heptane-3,7-dione-2-carboxylate to N-formimidoyl thienamycin utilizing the silylated derivative of N-formimidoyl cysteamine is described.

A PRACTICAL SYNTHESIS OF (+/-)-THIENAMYCIN

An efficient and operationally simply synthesis of (+/-)-thienamycin is described.

A facile transformation of bicyclic keto esters to bisprotected (±)-8-epithienamycin via enol activation

A facile "one-pot" transformation of bicyclic keto ester (2) to bisprotected (±)-8-epithienamycin via enol phosphate activation followed by the addition-elimination reaction of N-protected cysteamine derivative is described.