120316-01-0

Basic information

• Product Name: (R)-1-Benzyl-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3,3-difluoro-azetidin-2-one
• Synonyms: (R)-1-Benzyl-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3,3-difluoro-azetidin-2-one
• CAS NO: 120316-01-0
• Molecular Weight: 297.302
• Mol File: 120316-01-0.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (R)-1-Benzyl-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3,3-difluoro-azetidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-1-Benzyl-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3,3-difluoro-azetidin-2-one(120316-01-0)
• EPA Substance Registry System: (R)-1-Benzyl-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3,3-difluoro-azetidin-2-one(120316-01-0)

Safety Data

• Hazardous Substances Data: 120316-01-0(Hazardous Substances Data)

Upstream product

• 15186-48-8 2,3-isopropylidene-glyceraldehyde 
• 100-46-9 benzylamine 
• 100777-91-1 (2S)-2,3-O-isopropylideneglyceraldehyde N-benzylimine 
• 109872-87-9 methyl difluoroiodoacetate 
• 667-27-6 Ethyl bromodifluoroacetate 
• 683-98-7 methyl bromodifluoroacetate 

Downstream Products

• 120316-15-6 Acetic acid (2S,4R,5S)-5-acetoxy-4-benzylamino-3,3-difluoro-tetrahydro-pyran-2-yl ester 
• 120316-14-5 Acetic acid (2R,4R,5S)-5-acetoxy-4-benzylamino-3,3-difluoro-tetrahydro-pyran-2-yl ester 
• 147633-28-1 t-butyl (2R)-2-benzylamino-3,3-difluoro-4-hydroxybutanoate 
• 147730-78-7 (3R)-3-benzylamino-2,2-difluorobutane-1,4-diol 
• 135777-62-7 (4R)-1-benzyl-4-(t-butyloxycarbonyl)-3,3-difluoroazetidin-2-one 
• 147633-16-7 (4R)-1-benzyl-3,3-difluoro-4-<(1'S)-1',2'-dihydroxyethyl>azetidin-2-one 

Relevant articles and documents

Isopenicilin N synthase: A new mode of reactivity

Incubation of L-δ-(α-aminoadipoyl)-L-(3,3-difluorohomocysteinyl)-D-valine [an analogue of the natural substrate: L-δ-(α-aminoadipoyl)-L-(cysteinyl)-D-varine] with isopenicillin N synthase (IPNS) resulted in the production of a thiocarboxylic acid, i.e. both equivalents of the dioxygen cosubstrate were utilised to oxidise a single carbon of the cysteinyl analogue. This result and others are rationalised in terms of mechanistic proposals for the first ring closure by IPNS. The synthesis of L-difluorohomocysteine and related structures, via 3,3-difluoro-β-lactams, is described.