80951-83-3

Upstream product

• 82922-52-9 p-nitrobenzyl (5R,6S)-3-<(E)-2-acetamidoethylthio>-6-<(R)-1-formyloxyethyl>-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate 
• 1180012-46-7 (3S,4R)-benzyl N-(p-toluenesulfonyl)-3-((R)-1-(tert-butyldimethylsilyloxy)ethyl)-azetidin-2-one-4-carboxylate 
• 1180012-50-3 (3S,4R)-benzyl 3-((R)-1-(tert-butyldimethylsilyloxy)ethyl)-azetidin-2-one-4-carboxylate 
• 1190-73-4 2-(acetylamino)ethanethiol 
• 75321-08-3 p-nitrobenzyl (5R,6S)-2-diphenoxy phosphoryloxy-6-[(R)-1-hydroxyethyl]-1-carbapen-2-em-3-carboxylate 
• 76899-07-5 (3R,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one 
• 93788-48-8 4-nitrobenzyl 3-((tert-butyldimethylsilyl)oxy)-2-diazobut-3-enoate 
• 74288-39-4 (3S,4R)-3-[(R)-1-hydroxyethyl)-4-[3-(4-nitrobenzyl)oxycarbonyl-2-oxo-3-diazopropyl]azetidin-2-one 
• 115936-64-6 (3S,4R)-3-<(R)-1'-(dimethyl-t-butylsilyloxy)ethyl>-4-oxoazetidin-2-carboxylic acid 
• 74288-40-7 (5R,6S)-6-[(R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid p-nitrobenzyl ester 
• 93861-39-3 (3S,4R)-3-[(1R)-(tert-butyldimethyl-silyloxy)ethyl]-4-[3-(4-nitrobenzyloxy)carbonyl-2-oxo-3-diazopropyl]azetidin-2-one 

Downstream Products

• 73544-56-6 p-nitrobenzyl (5R,6R)-3-(2-acetamidoethylthio)-6-[(S)-1-methylsulphonyloxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate 
• 81488-32-6 (5R,6S)-6-((R)-1-Hydroxy-ethyl)-3-(1H-imidazol-4-ylmethylsulfanyl)-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.

β-Lactam antibiotics their preparation and their use

The present invention provides a process for inversion of the absolute stereochemistry at the α-carbon atom of a C-6 substituent of a bicyclic carbapenem antibiotic via a phosphorus - azodicarboxylate mediated reaction. Novel azides, amines and formates a

Inversion of Configuration at C-8 in the Olivanic Acids: Conversion into the Thienamycins and Other Novel Derivatives

The inversion of stereochemistry at C-8 in the olivanic acids, MM 22383 (7) and MM 22381 (6), is described.The reaction of p-nitrobenzyl (5R,6S)-3--6--7-oxo-1-azabicyclohept-2-ene-2-carboxylate (8) with diethyl azodicarboxylate, triphenylphosphine, and formic acid afforded the 6- derivative (17), which upon alkaline hydrolysis gave the 6- derivative (18).Hydrolysis of the p-nitrobenzyl ester (18) furnished the sodium salt of N-acetyldehydrothienamycin (15), the (8R)-epimer of the olivanic acid MM 22383 (7).The 3-(2-acetamidoethylthio)-analogue, MM 22381 (6), was converted into N-acetylthienamycin (14) by performing a similar series of reactions on its p-nitrobenzyl ester (10).The transformation of the ester (18) to bis-protected thienamycin (22), via the C-3 thiol (21), is also described.Reaction of the olivanic acid esters (8) and (10) with diethyl azodicarboxylate, triphenylphosphine and hydrazoic acid resulted in the formation of the 6- derivatives (27) and (28).Subsequent hydrolysis provided (5R,6R)-3--6--7-oxo-1-azabicyclohept-2-ene-2-carboxylic acid (29) and the 3-(2-acetamidoethylthio)-analogue (30).