101067-95-2

Upstream product

• 72658-09-4 (E)-(1-methoxyprop-1-enyloxy)trimethylsilane 
• 101067-92-9 Benzoic acid (R)-1-((2S,3R)-2-acetoxy-4-oxo-azetidin-3-yl)-ethyl ester 
• 101067-91-8 Benzoic acid (R)-1-((2R,3S)-2-acetyl-4-oxo-azetidin-3-yl)-ethyl ester 
• 101067-90-7 Benzoic acid (R)-1-((3S,4R)-2-oxo-4-trimethylsilanylethynyl-azetidin-3-yl)-ethyl ester 
• 65-85-0 benzoic acid 
• 279673-26-6 methyl (2Z,4E)-3-amino-2-methyl-2,4-hexadienoate 
• 279673-25-5 (2S,3S,3aS,4aS,5R,8S,8aR)-2,5,10,10-tetramethyl-octahydro-2H-5,8-methano-isoxazolo[3,2-b]benzoxazol-3-carbonitrile 
• 279673-27-7 methyl (2S,2'RS,3S,3'S,3aS,4aS,5R,8S,8aR)-3-(2,5,10,10-tetramethyl-ovtahydro-2H-5,8-methano-isoxazolo[3,2-b]benzoxazol-3-yl)-3'-amino-2'-methylpropanoate 
• 279673-24-4 methyl (2S,3S,3aS,4aS,5R,8S,8aR,2'Z)-3-(2,5,10,10-tetramethyloctahydro-2H-5,8-methano-isoxazolo[3,2-b]benzoxazol-3-yl)-3'-amino-2'-methyl-2'-propenoate 
• 279673-36-8 C₂₇H₃₈N₂O₆ 

Relevant academic research and scientific papers

Oxazoline N-oxide mediated [3+2] cycloadditions: Application to a formal synthesis of a (+)-β-methylcarbapenem

[3+2] Cycloaddition between a camphor-derived oxazoline N-oxide 9 and the γ,δ-unsaturated enamino ester 11 afforded the single adduct 6. A stereoselective reduction of the enamino ester side chain allowed the control of the absolute configuration of the two additional asymmetric centres. Nitrogen protection and oxidative hydrolysis of the resulting product 13, followed by further functional group manipulations, led to the β-lactam derivative 1, a known precursor of the β-methylthienamycin derivative 2a.

A FACILE, STEREOCONTROLLED ENTRY TO KEY INTERMEDIATES FOR THIENAMYCIN SYNTHESIS FROM ETHYL (S)-3-HYDROXYBUTANOATE

A new synthetic approach to optically active key intermediates for thienamycin synthesis is described which involves the highly stereocontrolled transformation of the 2-azetidinone obtained via the condensation of ethyl (S)-3-hydroxybutanoate with the N-s