101977-83-7

Basic information

• Product Name: (1'S,3S,4S)-3-(1'-<(tert-butyldimethylsilyl)oxy>ethyl)-1-(4'-methoxyphenyl)-4-(2'-phenylethenyl)-2-azetidinone
• Synonyms: (1'S,3S,4S)-3-(1'-<(tert-butyldimethylsilyl)oxy>ethyl)-1-(4'-methoxyphenyl)-4-(2'-phenylethenyl)-2-azetidinone
• CAS NO: 101977-83-7
• Molecular Weight: 437.654
• Mol File: 101977-83-7.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (1'S,3S,4S)-3-(1'-<(tert-butyldimethylsilyl)oxy>ethyl)-1-(4'-methoxyphenyl)-4-(2'-phenylethenyl)-2-azetidinone(CAS DataBase Reference)
• NIST Chemistry Reference: (1'S,3S,4S)-3-(1'-<(tert-butyldimethylsilyl)oxy>ethyl)-1-(4'-methoxyphenyl)-4-(2'-phenylethenyl)-2-azetidinone(101977-83-7)
• EPA Substance Registry System: (1'S,3S,4S)-3-(1'-<(tert-butyldimethylsilyl)oxy>ethyl)-1-(4'-methoxyphenyl)-4-(2'-phenylethenyl)-2-azetidinone(101977-83-7)

Safety Data

• Hazardous Substances Data: 101977-83-7(Hazardous Substances Data)

Upstream product

• 100009-52-7 3-(1-Hydroxy-ethyl)-1-(4-methoxy-phenyl)-4-((E)-styryl)-azetidin-2-one 
• 88315-63-3 (E)-4-methoxy-N-((E)-3-phenylallylidene)aniline 
• 101977-77-9 <3S,4S(E)>-3-<1(S)-hydroxyethyl>-1-(4-methoxyphenyl)-4-(2-phenylethenyl)-2-azetidinone 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 205525-21-9 (1'S,3S)-3-(1'-hydroxyethyl)-1-(4'-methoxyphenyl)-4-(2'-phenylethenyl)-2-azetidinone 
• 80542-40-1 N-cinnamylidene-p-anisidine 

Downstream Products

• 101989-66-6 (1'S,3S,4S)-3-(1'-<(tert-butyldimethylsilyl)oxy>ethyl)-4-formyl-1-(4'-methoxyphenyl)-2-azetidinone 
• 59995-64-1 thienamycin 
• 102046-00-4 (3S,4S)-1-(tert-Butyl-dimethyl-silanyl)-3-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-((E)-styryl)-azetidin-2-one 
• 102129-93-1 (1'S,3S,4R)-3-(1'-<(tert-butyldimethylsilyl)oxy>ethyl)-4-formyl-1-(4'-methoxyphenyl)-2-azetidinone 

Relevant articles and documents

Enantioselective lipase-catalyzed acetylation of β-lactam precursors of carbapenem antibiotics

The Amano PS-lipase-catalyzed enantioselective acetylation in vinyl acetate of (±)-3-hydroxyethyl-β-lactams 3-6, useful precursors of carbapenem antibiotics, proceeds with high enantioselectivity (E > 98) to afford the corresponding acetates 3b-6b in optically pure form. The rate of acetylation is influenced by the relative stereochemistry of the C(3)-C(4) β-lactam carbon atoms, the trans isomers being transformed much faster than the cis ones. The stereochemical preference of the lipase-PS is for the (1′R,3R) enantiomers, as determined by chemical correlation. On the other hand, the lipase-PS-catalyzed hydrolysis of esters 3b,d in phosphate buffer proceeds with low selectivity and at a lower rate.

3-(1'-hydroxyethyl)-2-azetidinones from 3-hydroxybutyrates and N-arylaldimines

Dianion imine addition, cyclisation reaction between ethyl-3-hydroxybutyrate and the aldimines generates β-lactams with the hydroxyethyl side chain of thienamycin and related β-lactam antibiotics in place. The effects of the N-arylaldimine and the reactio