94226-57-0

Basic information

• Product Name: Threonine, N,N-bis(phenylmethyl)-, methyl ester
• CAS NO: 94226-57-0
• Molecular Formula: C19H23NO3
• Molecular Weight: 313.397
• Mol File: 94226-57-0.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Threonine, N,N-bis(phenylmethyl)-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Threonine, N,N-bis(phenylmethyl)-, methyl ester(94226-57-0)
• EPA Substance Registry System: Threonine, N,N-bis(phenylmethyl)-, methyl ester(94226-57-0)

Safety Data

• Hazardous Substances Data: 94226-57-0(Hazardous Substances Data)

Upstream product

• 94226-55-8 (dibenzylamino)acetic acid methyl ester 
• 17360-47-3 N,N-dibenzylglycine 
• 75-07-0 acetaldehyde 
• 118965-94-9 (E) N,N'-dibenzyl-2-methoxy-2-trimethylsilyloxy-ethenamine 
• 102222-40-2 Dibenzyl-((Z)-2-methoxy-2-trimethylsilanyloxy-vinyl)-amine 
• 94226-77-4 2-Dibenzylamino-3-oxo-butyric acid methyl ester 

Downstream Products

• 876367-23-6 2-Dibenzylamino-3-hydroxy-butyric acid 

Relevant articles and documents

DIBENZYLAMINOACETATES AS USEFUL SYNTHETIC EQUIVALENTS OF GLYCINE IN THEi SYNTHESIS OF α-AMINO-β-HYDROXYACIDS

The stereochemical course of three new simple methodologies for the preparation of α-amino-β-hydroxyacids starting from dibenzylaminoacetates as synthetic equivalents of glycine is described.While the aldol-type condensation via lithium enolates gave results highly dependent on the aldehyde employed, producing in some cases diastereoselectivities up to 5:1 for the anti isomers, the acid-catalysed aldol condensation of silyl ketene acetals yielded predominantly syn adducts with selectivities from 5:1 to 32:1.Finally the acylation-reduction procedure gave the best results in terms of yields and stereoselectivities, affording syn isomers with excellent induction ( 13:1).

DIASTEREOSELECTIVE SYNTHESIS OF α-AMINO-β-HYDROXYACIDS

threo-α-Dibenzylamino-β-hydroxyesters (2) have been synthesised with high diastereoselectivity through the reduction of α-dibenzylamino-β-oxoesters (4) and then transformed into threo-α-amino-β-hydroxyacids.