87392-18-5

Upstream product

• 92686-04-9 <3R-<3α(R^*),4β>>-1-(2,4-dimethoxybenzyl)-3-(1-hydroxyethyl)-4-acetoxy-2-azetidinone 
• 81902-68-3 (2S,3R)-N-(2,4-dimethoxybenzyl)-N-(t-butoxycarbonylmethyl)-2,3-epoxybutyramide 
• 92685-93-3 <3R-<3α(R^*),4β>>-1-(2,4-dimethoxybenzyl)-3-(1-t-butyldimethylsilyloxyethyl)-4-acetoxy-2-azetidinone 
• 76899-07-5 (3R,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one 
• 86978-81-6 (3R,4R)-4-acetoxy-3-[(R)-1-(t-butyldimethylsilyloxy)ethyl]-1-trimethylsilyl-2-azetidinone 
• 81902-50-3 (2R,3R)-N-2,4-dimethoxybenzyl-N-bis(ethoxycarbonyl)methyl-2-bromo-3-acetoxybutylamide 
• 81902-51-4 <3S(R)>-1-(2,4-dimethoxybenzyl)-3-(1-acetoxyethyl)-4,4-bis(ethoxycarbonyl)-2-azetidinone 
• 81902-52-5 <3S-<3α(S^*),4α>>-1-(2,4-dimethoxybenzyl)-3-(1-acetoxyethyl)-4-ethoxycarbonyl-2-azetidinone-4-carboxylic acid 
• 81902-61-6 <3S-<3α(S^*),4β>>-t-butyl 1-(2,4-dimethoxybenzyl)-3-(1-t-butyldimethylsilyloxyethyl)-2-azetidinone-4-carboxylate 
• 81902-64-9 <3S-<3α(S^*),4β>>-1-(2,4-dimethoxybenzyl)-3-(1-t-butyldimethylsilyloxyethyl)-4-diazoacetyl-2-azetidinone 
• 81902-58-1 <3S-<3α(S^*),4β>>-1-(2,4-dimethoxybenzyl)-3-(1-t-butyldimethylsilyloxyethyl)-2-azetidinone-4-carboxylic acid chloride 
• 81902-57-0 <3S-<3α(S^*),4β>>-1-(2,4-dimethoxybenzyl)-3-(1-t-butyldimethylsilyloxyethyl)-2-azetidinone-4-carboxylic acid 
• 81902-59-2 (2S,3R)-N-(2,4-dimethoxybenzyl)-N-(t-butoxycarbonylmethyl)-2-bromo-3-hydroxybutyramide 
• 80829-72-7 <3S-<3α(S^*),4β>>-t-butyl 1-(2,4-dimethoxybenzyl)-3-(1-hydroxyethyl)-2-azetidinone-4-carboxylate 

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 
• 90628-99-2 p-nitrobenzyl (5R,6S)-6-<(R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-3-<<2-<<<(p-nitrobenzyl)oxy>carbonyl>-amino>ethyl>thio>-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate 
• 90628-97-0 3(S)-<1(R)-<(tert-butyldimethylsilyl)oxy>ethyl>-4(R)-<<<<2-<<(p-nitrobenzyloxy)carbonyl>amino>ethyl>thio>carbonyl>methyl>azetidin-2-one 
• 92133-37-4 [(2R,3S)-3-((R)-1-Hydroxy-ethyl)-4-oxo-azetidin-2-yl]-thioacetic acid S-[2-(4-nitro-benzyloxycarbonylamino)-ethyl] ester 
• 90628-91-4 (5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-isopropylsulfanyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester 
• 92133-38-5 (S)-3-{2-[(2R,3S)-3-((R)-1-Hydroxy-ethyl)-4-oxo-azetidin-2-yl]-acetylsulfanyl}-pyrrolidine-1-carboxylic acid 4-nitro-benzyl ester 
• 90628-89-0 {(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-isopropylsulfanylcarbonylmethyl-4-oxo-azetidin-1-yl}-oxo-acetic acid 4-nitro-benzyl ester 
• 98167-65-8 {(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-thioacetic acid S-((S)-1-{1-[(Z)-4-nitro-benzyloxycarbonylimino]-ethyl}-pyrrolidin-3-yl) ester 
• 90628-90-3 C₃₁H₅₁N₂O₁₀PSSi 
• 90629-06-4 (5R,6S)-3-[2-(4-Nitro-benzyloxycarbonylamino)-ethylsulfanyl]-7-oxo-6-((R)-1-trimethylsilanyloxy-ethyl)-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester 
• 90581-68-3 (5R,6S)-6-((R)-1-Hydroxy-ethyl)-3-((S)-1-{1-[(E)-4-nitro-benzyloxycarbonylimino]-ethyl}-pyrrolidin-3-ylsulfanyl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester 
• 90652-18-9 (5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-[(S)-1-(4-nitro-benzyloxycarbonyl)-pyrrolidin-3-ylsulfanyl]-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester 
• 90629-05-3 [(2R,3S)-2-[2-(4-Nitro-benzyloxycarbonylamino)-ethylsulfanylcarbonylmethyl]-4-oxo-3-((R)-1-trimethylsilanyloxy-ethyl)-azetidin-1-yl]-oxo-acetic acid 4-nitro-benzyl ester 
• 90628-98-1 {(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-[2-(4-nitro-benzyloxycarbonylamino)-ethylsulfanylcarbonylmethyl]-4-oxo-azetidin-1-yl}-oxo-acetic acid 4-nitro-benzyl ester 

Relevant academic research and scientific papers

Synthesis of 4-oxo-2-azetidineacetic acids by means of radical cyclization of N-vinylic α-bromo amides

Bu2SnH-mediated radical cyclization of α-bromo amide 8, bearing phenyl and phenylthio substituents at the terminus of the N-vinylic bond, proceeded in a 4-exo-trig manner to give β-lactam 9. Ruthenium tetroxide oxidation of the phenyl group incorporated into the product 9 provided a new synthesis of 4-oxo-2-azetidineacetic acid 13, a useful intermediate for (±)-PS-5. Chiral 4-oxo-2-azetidineacetic acids 23 and 36, key intermediates for the synthesis of (+)-PS-5 and (+)-thienamycin, respectively, were also obtained through the asymmetric radical cyclization of N-vinylic α-bromo amides having chiral auxillaries at the side-chain.

Chemistry of O-silylated ketene acetals: A stereoselective synthesis of optically active carbapenem antibiotics, (+)-thienamycin and (+)-PS-5

A stereoselective synthesis of the chiral thienamycin intermediate (16) involving a diastereoselective Michael addition and a silicon-induced Pummerer-type reaction is described. In a similar way, the key intermediate for (+)-PS-5 was also prepared from 4

STEREOSPECIFIC SYNTHESIS OF CHIRAL PRECURSORS OF THIENAMYCIN FROM L-THREONINE

L-Threonine was transformed, stereospecifically, to a versatile β-lactam (5a) in 3 steps.This β-lactam was further converted to a key intermediate (25) for the synthesis of thienamycin and its biologically active analogues.Furthermore, the compound 5a was changed to iodides (18 and 23), cyanides (19 and 24), chloromethylketone (26) and aldehydes (30 and 31) which appear to have a latent potential as precursors for the syntheses of the carbapenems.

AN EFFICIENT CARBAPENEM SYNTHESIS VIA AN INTRAMOLECULAR WITTIG REACTION OF NEW TRIALKOXYPHOSPHORANE-THIOLESTERS

New trialkoxyphosphorane-thiolesters 10, obtained by reaction of oxalimides 9 with trialkyl phosphite, were efficiently cyclized by an intramolecular Wittig reaction to give carbapenems 11.