76638-05-6

Basic information

• Product Name: methyl N-(2-methyl-3-phenyl-2(R),3(S)-epoxypropionyl)prolinate
• CAS NO: 76638-05-6
• Molecular Weight: 289.331
• Mol File: 76638-05-6.mol

Chemical Properties

• CAS DataBase Reference: methyl N-(2-methyl-3-phenyl-2(R),3(S)-epoxypropionyl)prolinate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl N-(2-methyl-3-phenyl-2(R),3(S)-epoxypropionyl)prolinate(76638-05-6)
• EPA Substance Registry System: methyl N-(2-methyl-3-phenyl-2(R),3(S)-epoxypropionyl)prolinate(76638-05-6)

Safety Data

• Hazardous Substances Data: 76638-05-6(Hazardous Substances Data)

Upstream product

• 124-41-4 sodium methylate 
• 63742-16-5 3(S)<1'(R)-bromophenylmethyl>-3(S)-methyl-1,4-dioxo-3,4,6,7,8a(S)-hexahydro-1H-pyrrolo<2,1-c><1,4>oxazine 
• 1895-97-2 2-methyl-3-phenylacrylic acid 
• 63742-09-6 1-((E)-2-methyl-3-phenyl-acryloyl)-L-proline 
• 5817-26-5 ethyl (2S)-pyrrolidine-2-carboxylate 

Downstream Products

• 76638-09-0 (2R,3S)-2-methyl-3-phenyloxirane-2-carbaldehyde 

Relevant articles and documents

ASYMMETRIC HALOLACTONISATION REACTION-4 ASYMMETRIC SYNTHESIS OF OPTICALLY ACTIVE α,β-EPOXYALDEHYDES FROM α,β-UNSATURATED ACIDS

The bromolactones (5) stereoselectively produced by the asymmetric bromolactonisation of (S)-N-(α,β-unsaturated)acylprolines (3), were elaborated to highly optically active 2(R),3(S)-epoxyaldehydes (8) (84-98percent ee) by successive epoxide formation and reductive cleavage of the proline moiety.The overall process constitutes a highly efficient asymmetric synthesis of 8 from α,β-unsaturated acids (1).

A highly efficient asymmetric synthesis of optically active α,β-epoxyaldehydes from α,β-unsaturated acids

The bromolactones(3) prepared from α,β-unsaturated acids(1) were converted to optically active α,β-epoxyaldehydes(2(R),3(S)-6)(84-98% ee) by successive epoxide formation and reductive cleavage of the proline moiety. The overall process constitutes a highly efficient asymmetric synthesis of 2(R),3(S)-6 from 1.