REVIEW (3R,4R)-4-Acetoxy-3-[(R)-1-(tert-butyldimethylsilyloxy) ethyl]azetidin-2-one is a key synthetic intermediate that has been extensively utilized in the synthesis of carbapenem and penam beta-lactam antibiotics. These have included thienamycin, faropenem, sulopenem and panipenem antibiotics.
REFERENCES
[1]
Chiba, Toshiyuki; Nakai, Takeshi An improved entry to a key intermediate for thienamycin synthesis from methyl (R)-3-hydroxybutanoate via direct epimerization at C-3 on 2-azetidinone rings Tetrahedron Letters (1985), 26(38), 4647-8.
[2]
Ito, Yoshio; Kawabata, Takeo; Terashima, Shiro A novel synthesis of (3R,4R)-4-acetoxy-3-[(R)-1-[(tert-butyldimethylsilyl)oxy]ethyl]-2-azetidinone, the versatile key intermediate of carbapenem synthesis, from (S)-ethyl lactate Tetrahedron Letters (1986), 27(47), 5751-4.
[3]
Endo, Masaki Practical synthesis of (3R,4R)-4-acetoxy-3-[1(R)-tert-butyldimethylsilyloxyethyl]azetidin-2-one. A key intermediate for penem and carbapenem synthesis Synthetic Communications (1987), 17(9), 1029-33.
[4]
Laurent, Mathieu; Ceresiat, Marcel; Marchand-Brynaert, Jacqueline Regioselective Baeyer-Villiger Oxidation in 4-Carbonyl-2-azetidinone Series: A Revisited Route toward Carbapenem Precursor Journal of Organic Chemistry (2004), 69(9), 3194-3197.
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