96035-98-2

Upstream product

• 3017-53-6 benzyl 2-bromopropionate 
• 76899-07-5 (3R,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one 
• 15082-42-5 lithium benzyloxide 
• 114418-63-2 (3S,4R)-3-<(R)-1-(t-Butyldimethylsilyloxy)ethyl>-4-<(S)-1-(4,4-dimethyl-2-oxazolidone-3-carbonyl)ethyl>-2-azetidinone 
• 102977-61-7 (3S,4R)-3-<(R)-1-(t-Butyldimethylsilyloxy)ethyl>-4-<(S)-1-((S)-4-isopropyl-2-oxazolidone-3-carbonyl)ethyl>-2-azetidinone 
• 114418-61-0 (3S,4R)-3-<(R)-1-(t-Butyldimethylsilyloxy)ethyl>-4-<(S)-1-((R)-4-phenyl-2-oxazolidone-3-carbonyl)ethyl>-2-azetidinone 
• 109616-59-3 (3S,4R)-3-<(R)-1-(t-Butyldimethylsilyloxy)ethyl>-4-<(S)-1-((S)-4-benzyl-2-oxazolidone-3-carbonyl)ethyl>-2-azetidinone 
• 100-39-0 benzyl bromide 
• 97101-07-0 (3S,4S)-3-<(1R)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-4-<(1S)-1-carboxyethyl>azetidin-2-one 
• 114341-78-5 (3S,4R)-3-<(R)-1-(t-Butyldimethylsilyloxy)ethyl>-4-<(R)-1-(2-oxazolidone-3-carbonyl)ethyl>-2-azetidinone 
• 114341-89-8 (3S,4R)-3-<(R)-1-(t-Butyldimethylsilyloxy)ethyl>-4-<(R)-1-(4,4-dimethyl-2-oxazolidone-3-carbonyl)ethyl>-2-azetidinone 
• 114341-95-6 (3S,4R)-3-<(R)-1-(t-Butyldimethylsilyloxy)ethyl>-4-<(R)-1-(4,4,5,5-tetramethyl-2-oxazolidone-3-carbonyl)ethyl>-2-azetidinone 
• 255837-99-1 (3S,4R)-3-<(R)-1-(t-Butyldimethylsilyloxy)ethyl>-4-<(R)-1-((S)-4-isopropyl-2-oxazolidone-3-carbonyl)ethyl>-2-azetidinone 
• 109715-77-7 (3S,4R)-3-<(R)-1-(t-Butyldimethylsilyloxy)ethyl>-4-<(R)-1-((S)-4-benzyl-2-oxazolidone-3-carbonyl)ethyl>-2-azetidinone 

Downstream Products

• 105370-87-4 (3S,4S)-4-<(1S)-1-benzyloxycarbonylethyl>1-(tert-butoxycarbonylmethyl)-3-<(1R)-1-tert-butyldimethylsilyloxy>-2-azetidinone 
• 93711-85-4 (2R)-2-[(2S,3S)-3-{(1R)-1-(t-butyldimethylsilyloxy)ethyl}-4-oxoazetidin-2-yl]propionic acid 
• 135038-17-4 (R)-benzyl 2-((2S,3S)-3-((R)-1-hydroxyethyl)-4-oxoazetidin-2-yl)propanoate 
• 135096-42-3 (R)-benzyl 2-((2S,3S)-3-((1S)-1-hydroxyethyl)-4-oxoazetidin-2-yl)propanoate 
• 97101-07-0 (3S,4S)-3-<(1R)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-4-<(1S)-1-carboxyethyl>azetidin-2-one 
• 105318-31-8 (3S,4S)-3-<(1R)-1-tert-butyldimethylsilyloxythyl>-1-(p-nitrobenzyloxycarbonylmethyl)-4-<(1R)-1-phenylthiocarbonylethyl>-2-azetidinone 
• 105318-30-7 (3S,4S)-3-<(1R)-1-hydroxyethyl>-1-(p-nitrobenzyloxycarbonylmethyl)-4-<(1R)-1-phenylthiocarbonylethyl>-2-azetidinone 
• 105318-06-7 (3S,4S)-1-(tert-butoxycarbonylmethyl)-3-<(1R)-1-tert-butyldimethylsilyloxyethyl>-4-<(1R)-1-phenylthiocarbonylethyl>-2-azetidinone 
• 105318-23-8 (3S,4S)-3-[(1R)-1-hydroxyethyl]-4-[(1R)-1-phenylthiocarbonylethyl]-1-carboxymethylazetidin-2-one 

Relevant academic research and scientific papers

CARBAPENEM COMPOUNDS

This invention relates to carbapenem compounds, their stereoisomers, pharmaceutically acceptable salts or N-oxides thereof, which may be useful for the treatment of bacterial infections, particularly drug-resistant bacterial infections, as well as the pro

Synthetic studies of carbapenem and penem antibiotics. V. Efficient synthesis of the 1β-methylcarbapenem skeleton

An efficient synthesis of 1β-methylcarbapenem from the 1-(2- oxoazetidinyl)acetate 8 was developed by application of the Dieckmann reaction. Dieckmann-type cyclization of 8 and conversion to the enolphosphate 10 were achieved without epimerization to the 1α-methyl isomer in a one-pot procedure. Treatment with the mercaptan 22 after the phosphorylation resulted in a practical one-pot preparation of the 1β-methylcarbapenem derivative 23 from 8.

Highly stereocontrolled synthesis of the 1β-methylcarbapenem key intermediate by the Reformatsky reaction of 3-(2-bromopropionyl)-2-oxazolidone derivatives with a 4-acetoxy-2-azetidinone

The key synthetic intermediate (4) of 1β-methylcarbapenems (1~3) was efficiently synthesized by employing highly stereocontrolled Reformatsky reaction (C4-alkylation) of 3-(2-bromopropionyl)-2-oxazolidone derivatives (6) with (3R,4R)-4-acetoxy-3-[(R)-1-(t-butyldimethylsilyloxy)ethyl]-2-azetidino ne (5) in the presence of zinc dust followed by removal of 2-oxazolidone moieties. The best diastereoselectivity (β:α = 95:5) could be realized by uses of sterically crowded achiral 2-oxazolidone derivatives such as 4,4-dimethyl-, 4,4,5,5-tetramethyl, and 4,4-dibutyl-5,5-pentamethylene-2-oxazolidone and higher reaction temperatures (refluxing tetrahydrofran). The remarkable diastereoselectivities observed for the Reformatsky reactions could be explained by means of the weakly chelating transition state models.