76855-69-1 (3R,4R)-4-Acetoxy-3-[(R)-1-(tert-butyldimethylsilyloxy) ethyl]azetidin-2-one AKSci K330
 
 
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  K330    
(3R,4R)-4-Acetoxy-3-[(R)-1-(tert-butyldimethylsilyloxy) ethyl]azetidin-2-one
, 98% (HPLC)
 
[3R(1'R,4R)]-(+)-4-Acetoxy-3-[1-(tert-butyldimethylsilyloxy)ethyl]-2-azetidinone




IDENTITY
CAS Number:76855-69-1
MDL Number:MFCD00077636
MF:C13H25NO4Si
MW:287.43
EINECS:408-050-9
SPECIFICATIONS & PROPERTIES
Purity:98% (HPLC)
Spectra:LCMS, HPLC, Polarimetry
Physical Form:White to off-white powder
Melting Point:107-111°C
Optical Rotation:+48.0° - +53.0° (c=1, CHCl3)
Long-Term Storage:Store long-term at 2-8°C

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.

GHS

Pictograms

Signal Word
Warning

Hazard Statements
H317; H319; H411

Precautionary Statements
P261; P264; P272; P273; P280; P302+P352; P305+P351+P338; P333+P313; P337+P313; P363; P391; P501


Current as of July 7, 2020


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CATEGORIES

 APIs and Bioactives > beta-Lactams


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