139345-06-5

Basic information

• Product Name: (3R,3aR,4S,6aR,4'S)-2-benzyl-3(2,2-dimethyl-1,3-dioxolan-4-yl)-4-phenyl-hexahydro-4H-phospholo<2,3-d>isoxazole 4-oxide
• CAS NO: 139345-06-5
• Molecular Weight: 413.453
• Mol File: 139345-06-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (3R,3aR,4S,6aR,4'S)-2-benzyl-3(2,2-dimethyl-1,3-dioxolan-4-yl)-4-phenyl-hexahydro-4H-phospholo<2,3-d>isoxazole 4-oxide(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,3aR,4S,6aR,4'S)-2-benzyl-3(2,2-dimethyl-1,3-dioxolan-4-yl)-4-phenyl-hexahydro-4H-phospholo<2,3-d>isoxazole 4-oxide(139345-06-5)
• EPA Substance Registry System: (3R,3aR,4S,6aR,4'S)-2-benzyl-3(2,2-dimethyl-1,3-dioxolan-4-yl)-4-phenyl-hexahydro-4H-phospholo<2,3-d>isoxazole 4-oxide(139345-06-5)

Safety Data

• Hazardous Substances Data: 139345-06-5(Hazardous Substances Data)

Upstream product

• 91190-38-4 N-benzyl-2,3-O-isopropylidene-D-glyceraldehyde nitrone 
• 703-03-7 1-phenyl-2-phospholene-1-oxide 

Relevant articles and documents

Nitrone Cycloadditions to 2,3-Dihydro-1-phenyl-1H-phosphole 1-Oxide. Double Asymmetric Induction and Kinetic Resolution by a Chiral Nitrone

The cycloadditions of nitrones with 2,3-dihydro-1-phenyl-1H-phosphole 1-oxide give a single cycloadduct deriving from a highly diastereoselective approach of the nitrone anti to the phenyl ring of phospholene oxide.When the chiral gliceraldehyde derived nitrone is used, only two diastereoisomers are produced in 1.7:1 ratio.The structural assignment based on NMR data and X-ray analysis of the major isomer established a trans C3-C4 stereochemistry (derived from endo TS with respect to nitrone) and a C3-C4' relative stereochemistry of threo type in the major isomer and erythro in the minor one.Therefore, each enantiomer of phospholene oxide 6 gives exclusively one cycloadduct with five contiguous stereogenic centres in an established and predictable absolute configuration.The difference of reactivity of the two enantiomers allowed a partial kinetic resolution of the racemic phospholene oxide, affording (+)-(S) enantiomer with 90percent enantiomeric excess.