96035-98-2Relevant articles and documents
CARBAPENEM COMPOUNDS
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Page/Page column 52, (2017/10/13)
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
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
Ito,Sasaki,Tamoto,Sunagawa,Terashima
, p. 2801 - 2820 (2007/10/02)
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.
Syntheses of chiral intermediates of 1-β-methylcarbapenems: (3S,4R)-3-[1(R)-tert-butyldimethylsilyloxyethyl]-4-chloroazetidin-2-one and yldimethylsilyloxyethyl]-4-[1(R)-tert-butylthiocarbonylethyl]azetidin-2-one
Endo
, p. 2140 - 2145 (2007/10/02)
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