154129-97-2

Upstream product

• 154129-93-8 (1R,2S)-2-(N-tert-butoxycarbonyl)benzylamino-4-methyl-1-(1,3-thiazol-2-yl)pentyl acetate 
• 61-90-5 L-leucine 
• 75691-28-0 methyl (S)-2-(benzylideneamino)-4-methylpentanoate 
• 66399-70-0 N-benzyl-L-leucine methyl ester 
• 154129-74-5 (S)-methyl 2-(benzyl(tert-butoxycarbonyl)amino)-4-methylpentanoate 
• 154129-75-6 2-(N-benzyl-N-tert-butoxycarbonylleucyl)-1,3-thiazole 
• 154129-80-3 (1'R,2'S)-2-<2-(N-benzyl-N-tert-butoxycarbonylamino)-1-hydroxy-4-methylpentyl>-1,3-thiazole 

Relevant academic research and scientific papers

2-Thiazolyl α-amino ketones: A new class of reactive intermediates for the stereocontrolled synthesis of unusual amino acids

The thiazole-based one carbon homologation of four α-amino acids (L-phenylalanine, L-leucine, L-threonine, and L-serine) to the corresponding α-hydroxy β-amino aldehydes and acids in both configurations at C(α), is described. The methodology involves the following key operations: (i) the conversion of an α-amino ester to a 2-thiazolyl α-amino ketone; (ii) the stereocontrolled reduction of a ketone carbonyl to either syn or anti α,β-amino alcohols; (iii) the aldehyde release from the thiazole ring; (iv) the oxidation of the aldehyde to a carboxylic acid. The methodology was only partially applied to L-phenylglycine because of some limitations in operation (i).