351074-49-2

Upstream product

• 160237-99-0 (3R,4S)-1-(4-methoxyphenyl)-3-(benzyloxy)-4-(hydroxymethyl)-2-azetidinone 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 160237-98-9 (3R,4S)-1-(4-methoxyphenyl)-3-(benzyloxy)-4-vinyl-2-azetidinone 
• 115857-84-6 (3R,4S)-3-(Benzyloxy)-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>-1-(4-methoxyphenyl)azetidin-2-one 
• 160334-80-5 (-)-(3R,4S)-trans-3-benzyloxy-4-formyl-1-(p-methoxyphenyl)-2-azetidinone 
• 148968-08-5 (+)-(3R,4R)-1-(p-anisyl)-3-benzyloxy-4-formyl-2-azetidinone 

Downstream Products

• 351074-56-1 methyl (2Z,4S,5S)-4-benzyloxy-5-[(tert-butyloxycarbonyl)amino]-6-({[tert-butyl(diphenyl)silyl]oxy}methyl)-2-hexenoate 
• 351074-52-7 (-)-(2R,3S)-2-benzyloxy-3-[(tert-butyloxycarbonyl)amino]-4-({[tert-butyl(diphenyl)silyl]oxy}methyl)butan-1-ol 
• 351074-50-5 (+)-(3R,4S)-1-(tert-butyloxycarbonyl)-3-benzyloxy-4-({[tert-butyl(diphenyl)silyl]oxy}methyl)-2-azetidinone 
• 351074-54-9 (2R,3S)-2-benzyloxy-3-[(tert-butyloxycarbonyl)amino]-4-({[tert-butyl(diphenyl)silyl]oxy}methyl)butanal 
• 351074-58-3 (+)-(5S,6S)-5-benzyloxy-6-({[tert-butyl(diphenyl)silyl]oxy}methyl)-1,2,5,6-tetrahydro-2-pyridinone 
• 614733-12-9 (-)-(3R,4S)-3-benzyloxy-4-({[tert-butyl(diphenyl)silyl]oxy}methyl)-2-azetidinone 

Relevant academic research and scientific papers

Facile conversion of 2-azetidinones to 2-piperidones: Application to a formal synthesis of Prosopis and Cassia alkaloids

Nonracemic 5,6-disubstituted 2-piperidones were prepared from readily accessible 3,4-disubstituted-2-azetidinones having pre-installed substituents by reductive ring opening of 2-azetidinones followed by stereoselective installation of Z-α,β-unsaturated ester and lactam formation. For the synthetic application to the naturally occurring piperidine alkaloids, such as Prosopis and Cassia alkaloids, 5-hydroxy-2-piperidones (+)-13 and (-)-24 were prepared from 2-azetidinones (-)-6b and (+)-18 via two-carbon ring homologation.

Facile transformation of 3,4-disubstituted 2-azetidinones to chiral 5,6-dihydro-2-pyridones

Chiral 5,6-disubstituted-5,6-dihydro-2(1H)-pyridones were prepared efficiently from readily accessible 3,4-disubstituted-2-azetidinones having preadjusted substituents and stereochemistry through the reductive ring opening of 2-azetidinones followed by Z-selective installation of acetate moiety and re-cyclization to 2-pyridones.