106819-63-0

Upstream product

• 85-44-9 phthalic anhydride 
• 39994-75-7 L-threonine methyl ester hydrochloride 
• 3373-59-9 L-threonine methyl ester 

Downstream Products

• 106763-29-5 (2S,3S)-β-Methyl-N-phthaloylphenylalanin-methylester 
• 112424-23-4 N-Phthaloyl-vinylglycin-methylester 
• 112424-22-3 N-Phthaloyl-2,3-didehydroalanin-methylester 
• 112458-67-0 (2S,3S)-β-Methyl-N-phthaloyl-β-(2,5-dimethoxyphenyl)alanin-methylester 
• 112458-66-9 (2S,3S)-β-Methyl-N-phthaloylmesitylalanin-methylester 
• 106763-31-9 (2S,3R)-β-Methyl-N-phthaloylphenylalanin-methylester 
• 75-07-0 acetaldehyde 

Relevant academic research and scientific papers

Halofluorination of N-protected α,β-dehydro-α-amino acid esters—A convenient synthesis of α-fluoro-α-amino acid derivatives

N-protected dehydroamino acid methyl esters have been converted to α-fluoro-β-halo amino acid derivatives under halofluorination reaction conditions. The influences of the nitrogen protecting group of the substrates and of the halonium electrophile on the reaction outcome and the stability of the obtained products have been studied. Furthermore, reduction of the halogen substituent (Cl or Br) under radical conditions provided a possibility for follow-up reactions. Nucleophilic substitution reactions, however, failed.

Stereoselective syntheses of 4-oxa diaminopimelic acid and its protected derivatives via aziridine ring opening

Regio- and stereoselective aziridine ring opening with oxygen nucleophiles derived from serine and threonine provides a route to stereochemically pure 4-oxa-2,6-diaminopimelic acid (oxa-DAP) and its methyl-substituted derivatives. Oxa-DAP is a substrate of DAP epimerase, a key enzyme for biosynthesis of L-lysine and formation of peptidoglycan precursors. Orthogonally protected analogues of lanthionine and/β-methyllanthionine wherein oxygen replaces sulfur were prepared that could be used for solid-supported peptide synthesis to make oxa derivatives of lantibiotics.