87238-52-6

Usage

InChI:InChI=1/C13H16N2O8S/c1-5(16)8-10(18)15-9(12(19)23-4-22-6(2)17)7(24-11(8)15)3-21-13(14)20/h5,8,11,16H,3-4H2,1-2H3,(H2,14,20)/t5-,8+,11-/m1/s1

Upstream product

• 104128-21-4 (5R,6S)-3-Carbamoyloxymethyl-7-oxo-6-((R)-1-trimethylsilanyloxy-ethyl)-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid acetoxymethyl ester 
• 92445-71-1 acetoxymethyl(5R,6S)-2-carbamoyloxymethyl-6-[1(R)-trichloroethoxycarbonyloxyethyl]-penem-3-carboxylate 
• 127657-62-9 (5R,6S)-6-Bromo-3-carbamoyloxymethyl-6-((R)-1-hydroxy-ethyl)-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid acetoxymethyl ester 
• 138471-46-2 (5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-carbamoyloxymethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid acetoxymethyl ester 
• 92445-69-7 2-{(2R,3S)-2-(1-Carbamoyloxymethyl-vinylsulfanyl)-4-oxo-3-[(R)-1-(2,2,2-trichloro-ethoxycarbonyloxy)-ethyl]-azetidin-1-yl}-3-methyl-but-2-enoic acid acetoxymethyl ester 
• 104128-20-3 [(2R,3S)-2-(2-Carbamoyloxy-acetylsulfanyl)-4-oxo-3-((R)-1-trimethylsilanyloxy-ethyl)-azetidin-1-yl]-oxo-acetic acid acetoxymethyl ester 
• 104128-17-8 2-[(2R,3S)-2-(2-Carbamoyloxy-acetylsulfanyl)-4-oxo-3-((R)-1-trimethylsilanyloxy-ethyl)-azetidin-1-yl]-3-methyl-but-2-enoic acid acetoxymethyl ester 
• 104128-15-6 2-[(2R,3S)-2-(Benzothiazol-2-yldisulfanyl)-4-oxo-3-((R)-1-trimethylsilanyloxy-ethyl)-azetidin-1-yl]-3-methyl-but-2-enoic acid acetoxymethyl ester 
• 92445-68-6 2-{(2R,3S)-2-(3-Hydroxy-prop-1-ene-2-sulfinyl)-4-oxo-3-[(R)-1-(2,2,2-trichloro-ethoxycarbonyloxy)-ethyl]-azetidin-1-yl}-3-methyl-but-2-enoic acid acetoxymethyl ester 
• 121230-16-8 2-[(R)-2-(2-Carbamoyloxy-acetylsulfanyl)-3-((R)-1-hydroxy-ethyl)-4-oxo-azetidin-1-yl]-3-methyl-but-2-enoic acid acetoxymethyl ester 
• 138450-69-8 acetoxymethyl oxalic acid 
• 138450-70-1 Chloro-oxo-acetic acid acetoxymethyl ester 
• 138450-68-7 acetoxymethyl glycolate 

Downstream Products

• 84845-57-8 ritipenem 

Relevant academic research and scientific papers

A NEW REDUCTIVE ACYLATION OF AZETIDINONE DISULPHIDE IN THE ROUTE TO PENEMS

The use of triethyl phosphite and the appropriate carboxylic anhydride was found to constitute an efficient method for the conversion of azetidinyl benzthiazolyl disulphides into acylthioazetidinones, allowing a short synthesis of penem FCE 22891 from its penam-1-oxide precursor.

The total synthesis of ritipenems. Construction of penem thiazoline ring by incorporation of two 2C units of glycolic acid

Short syntheses of ritipenem acoxyl 1a and ritipenem 1b are reported. The syntheses start from (R)-4-acetoxy-(S)-3-[(R)-1-(t-butyldimethylsilyloxy)ethyl]azetidin-2-o ne 3 and are based on the incorporation of two 2C unites obtained by manipulation of glicolyc acid 4.

ZINC MEDIATED REDUCTION OF BROMOHYDRINS IN AZETIDINONES AND PENEMS. APPLICATION TO THE SYNTHESIS OF FCE 22891

A route to penems is described in which dehalogenative reduction of bromohydrins is carried out after ring opening of the penam nucleus.Reduction on some newly synthesized bromopenems suffered from low yields.Better yields and acceptable steroselectivity were obtained on free-hydroxyethyl azetidinone substrates.Some parameters of the reduction are discussed.

Process for the preparation of penems

A process for preparing 2-methyl substituted penems useful as antibiotics agent and/or as intermediates thereof, by reacting an appropriate 1-imido-3,4-disubstituted azetidinone derivative with a trivalent organophosphorus compound in an inert solvent at a temperature of from 110° to 150° C. for a period of from 2 hours to a few days.

A NEW ROUTE TO PENEMS AND CARBAPENEMS

A new ring closure by carbonyl-carbonyl reductive coupling is utilized in the synthesis of penem and carbapenem nuclei.