101905-26-4

Basic information

• Product Name: (1'R,3S,4R)-3-<1'-((tert-butyldimethylsilyl)oxy)ethyl>-1-(4'-methoxyphenyl)-4-(2'-phenylethenyl)-2-azetidinone
• Synonyms: (1'R,3S,4R)-3-<1'-((tert-butyldimethylsilyl)oxy)ethyl>-1-(4'-methoxyphenyl)-4-(2'-phenylethenyl)-2-azetidinone
• CAS NO: 101905-26-4
• Molecular Weight: 437.654
• Mol File: 101905-26-4.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (1'R,3S,4R)-3-<1'-((tert-butyldimethylsilyl)oxy)ethyl>-1-(4'-methoxyphenyl)-4-(2'-phenylethenyl)-2-azetidinone(CAS DataBase Reference)
• NIST Chemistry Reference: (1'R,3S,4R)-3-<1'-((tert-butyldimethylsilyl)oxy)ethyl>-1-(4'-methoxyphenyl)-4-(2'-phenylethenyl)-2-azetidinone(101905-26-4)
• EPA Substance Registry System: (1'R,3S,4R)-3-<1'-((tert-butyldimethylsilyl)oxy)ethyl>-1-(4'-methoxyphenyl)-4-(2'-phenylethenyl)-2-azetidinone(101905-26-4)

Safety Data

• Hazardous Substances Data: 101905-26-4(Hazardous Substances Data)

Upstream product

• 88315-63-3 (E)-4-methoxy-N-((E)-3-phenylallylidene)aniline 
• 141781-29-5 S-2-Pyridyl (R)-3-tert-butyldimethylsilyloxybutanoate 
• 80542-40-1 N-cinnamylidene-p-anisidine 
• 104-94-9 4-methoxy-aniline 
• 14371-10-9 (E)-3-phenylpropenal 
• 100009-52-7 3-(1-Hydroxy-ethyl)-1-(4-methoxy-phenyl)-4-((E)-styryl)-azetidin-2-one 
• 205525-21-9 (1'S,3S)-3-(1'-hydroxyethyl)-1-(4'-methoxyphenyl)-4-(2'-phenylethenyl)-2-azetidinone 
• 18162-48-6 tert-butyldimethylsilyl chloride 

Downstream Products

• 203252-14-6 (2R,3R)-3-((R)-1-(tert-butyldimethylsilyloxy)ethyl)-1-(4-methoxyphenyl)-4-oxoazetidin-2-yl acetate 
• 97363-07-0 (2S,3S)-3-((R)-1-((tert-butyldimethylsilyl)oxy)ethyl)-1-(4-methoxyphenyl)-4-oxoazetidine-2-carboxylic acid 
• 76899-07-5 (3R,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one 
• 101905-27-5 (1'R,3S,4R)-3-<1'-((tert-butyldimethylsilyl)oxy)ethyl>-4-(2'-phenylethenyl)-2-azetidinone 
• 106399-62-6 (1'R,3S,4S)-3-(1'-(tert-butyldimethylsilyloxy)ethyl)-4-formyl-1-(4'-methoxyphenyl)-2-azetidinone 

Relevant articles and documents

Stereo- and Enantio-controlled Synthesis of Chiral Intermediates for the Total Synthesis of Thienamycin and Related β-Lactam Antibiotics from 3-Hydroxybutyrates

The synthesis of (1'R,3S,4S)- and (1'R,3S,4R)-3-(1'-t-butyldimethylsilyloxyethyl)-4-hydroxymethyl-2-azetidinone from ethyl (S)-3-hydroxybutyrate is reported.

Synthesis of β-lactams by condensation of titanium enolates of 2-pyridylthioesters with imines. Influence of the imine structure on the trans/cis stereoselectivity

The condensation of the titanium enolates of C-2 alkyl substituted 2-pyridylthioesters with imines affords β-lactams in trans/cis ratios that largely depend on the structure of the C-imine residue. Bulky and non-chelating heteroatom-containing groups lead to the formation of trans β-lactams, while sterically non-requiring or chelating groups favour the formation of the cis-products. On the basis of NMR evidences a rationale is proposed to account for the observed stereoselectivity.

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