934237-45-3

Basic information

• Product Name: tert-butyl (3S,5S)-5-hydroxy-3-phenylisoxazolidine-2-carboxylate
• Synonyms: tert-butyl (3S,5S)-5-hydroxy-3-phenylisoxazolidine-2-carboxylate
• CAS NO: 934237-45-3
• Molecular Weight: 265.309
• Mol File: 934237-45-3.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: tert-butyl (3S,5S)-5-hydroxy-3-phenylisoxazolidine-2-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl (3S,5S)-5-hydroxy-3-phenylisoxazolidine-2-carboxylate(934237-45-3)
• EPA Substance Registry System: tert-butyl (3S,5S)-5-hydroxy-3-phenylisoxazolidine-2-carboxylate(934237-45-3)

Safety Data

• Hazardous Substances Data: 934237-45-3(Hazardous Substances Data)

Upstream product

• 36016-38-3 tert-Butyl N-hydroxycarbamate 
• 104-55-2 3-phenyl-propenal 
• 14371-10-9 (E)-3-phenylpropenal 

Downstream Products

• 135865-78-0 tert-butyl (1S)-3-oxo-1-phenylpropylcarbamate 

Relevant articles and documents

Immobilization of cis-4-Hydroxydiphenylprolinol Silyl Ethers onto Polystyrene. Application in the Catalytic Enantioselective Synthesis of 5-Hydroxyisoxazolidines in Batch and Flow

A new family of polystyrene-supported cis-4-hydroxydiphenylprolinol silyl ethers has been prepared, and the resulting polymers have been evaluated as organocatalysts to promote the tandem reaction between N-protected hydroxylamines and α,β-unsaturated aldehydes in batch and flow. The new PS-supported catalysts compare favorably with well-established immobilized J?rgensen-Hayashi catalysts, affording 5-hydroxyisoxazolidines as single diastereoisomers with high enantioselectivities and good yields (up to 83% yield, up to 99% ee). (Figure presented.).

Catalytic enantioselective 5-hydroxyisoxazolidine synthesis: An asymmetric entry to β-amino acids

The highly chemo- and enantioselective organocatalytic tandem reaction between N-carbamate-protected hydroxylamines and α,β-unsaturated aldehydes is presented. The reaction represents a unique entry for the asymmetric synthesis of 5-hydroxyisoxazolidines, oxazolidin-5-ones or γ-hydroxyamino alcohols in high yields and 90-99% ee. A procedure for the conversion of the oxazolidin-5-ones into the corresponding β-amino acids is also described. Georg Thieme Verlag Stuttgart.