101905-27-5

Basic information

• Product Name: (1'R,3S,4R)-3-<1'-((tert-butyldimethylsilyl)oxy)ethyl>-4-(2'-phenylethenyl)-2-azetidinone
• Synonyms: (1'R,3S,4R)-3-<1'-((tert-butyldimethylsilyl)oxy)ethyl>-4-(2'-phenylethenyl)-2-azetidinone
• CAS NO: 101905-27-5
• Molecular Weight: 331.53
• Mol File: 101905-27-5.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (1'R,3S,4R)-3-<1'-((tert-butyldimethylsilyl)oxy)ethyl>-4-(2'-phenylethenyl)-2-azetidinone(CAS DataBase Reference)
• NIST Chemistry Reference: (1'R,3S,4R)-3-<1'-((tert-butyldimethylsilyl)oxy)ethyl>-4-(2'-phenylethenyl)-2-azetidinone(101905-27-5)
• EPA Substance Registry System: (1'R,3S,4R)-3-<1'-((tert-butyldimethylsilyl)oxy)ethyl>-4-(2'-phenylethenyl)-2-azetidinone(101905-27-5)

Safety Data

• Hazardous Substances Data: 101905-27-5(Hazardous Substances Data)

Upstream product

• 106399-98-8 (1'R*,3R*,4S*)-3-[1'-(tert-Butyldimethylsilyloxy)ethyl]-1-(4'-methoxyphenyl)-4-(2'-phenylethenyl)azetidin-2-one 
• 14371-10-9 (E)-3-phenylpropenal 
• 141781-29-5 S-2-Pyridyl (R)-3-tert-butyldimethylsilyloxybutanoate 
• 80542-40-1 N-cinnamylidene-p-anisidine 
• 205525-21-9 (1'S,3S)-3-(1'-hydroxyethyl)-1-(4'-methoxyphenyl)-4-(2'-phenylethenyl)-2-azetidinone 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 88315-63-3 (E)-4-methoxy-N-((E)-3-phenylallylidene)aniline 
• 101905-26-4 (1'R,3S,4R)-3-<1'-((tert-butyldimethylsilyl)oxy)ethyl>-1-(4'-methoxyphenyl)-4-(2'-phenylethenyl)-2-azetidinone 

Downstream Products

• 96790-00-0 (1'S,3S,4R)-3-(1'-Hydroxyethyl)-4-(2'-phenylethenyl)-azetidin-2-one 

Relevant articles and documents

Soluble-polymer-supported synthesis of β-lactams on a modified poly(ethylene glycol)

A modified poly(ethylene glycol) (PEG) has been developed for the soluble-polymer-supported synthesis of β-lactams. The monomethylether of PEG (MeOPEG) with an average Mw of 5000 was used as the support, a 4-(3-propyl)phenyl residue as the spacer, and a 4-oxyphenylamino group as the moiety with the reactive functionality. From this modified PEG representative aromatic, heteroaromatic, unsaturated, and aliphatic imines were obtained in high yields by different procedures. The polymer-supported imines were then employed to prepare several β-lactams by enolate/imine condensation and ketene/ imine cycloaddition. Examples of the control of the absolute stereochemistry during the azetidinone ring formation are also reported. The reactions carried out on the polymer-bound imines showed a remarkable similarity to those performed on nonimmobilized imines, both in terms of yields and stereoselectivities. Removal of the β-lactams from the polymer has also been accomplished to directly deliver the N-unsubstituted azetidinones.

ANODIC N-DEARYLATION OF 2-AZETIDINONES

N-Methoxyphenyl-2-azetidinones are dearylated under mild conditions via anodic oxidation

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.