154130-17-3

Upstream product

• 79265-30-8 2-(trimethylsilyl)thiazole 
• 143978-88-5 N-tert-butoxycarbonyl-L-phenylglycine methyl ester 
• 2900-27-8 (2S)-2-[(tert-butoxycarbonyl)amino]-2-phenylethanoic acid 
• 15028-39-4 L-2-phenylglycine methyl ester hydrochloride 
• 2935-35-5 (S)-2-phenylglycine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 154130-16-2 ((S)-2-Oxo-1-phenyl-2-thiazol-2-yl-ethyl)-carbamic acid tert-butyl ester 

Downstream Products

• 154130-21-9 methyl (S,S)-2-acetoxy-3-tert-butoxycarbonylamino-3-phenylpropionate 
• 154130-20-8 (S,S)-2-acetoxy-3-tert-butoxycarbonylamino-3-phenylpropanal 
• 154130-19-5 (S,S)-2-tert-butoxycarbonylamino-2-phenyl-1-(1,3-thiazol=2-yl)ethyl acetate 

Relevant academic research and scientific papers

Synthesis of taxol and taxotere side chains by 2-(trimethylsilyl)thiazole based homologation of L-phenylglycine

L-Phenylglycine is homologated by the use of 2-(trimethylsilyl)thiazole into (2R,3S)-N-benzoyl- and N-tert-butoxycarbonyl-3-phenylisoserine, which are isolated as acetonide derivatives in 47 and 35% overall yields and with 84 and 90% ee, respectively.

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).