224321-02-2

Upstream product

• 540-88-5 acetic acid tert-butyl ester 
• 89625-39-8 (2S,4R)-N-(benzyloxycarbonyl)-4-acetoxyproline 
• 13504-85-3 (2S,4R)-1-(benzyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid 

Downstream Products

• 72289-52-2 (2S,4R)-4-hydroxy-1-phenylmethoxycarbonylpyrrolidine-2-carboxylic acid tert-butyl ester 

Relevant academic research and scientific papers

The synthesis of bicyclic proline derivatives with 1,4N-lactam grouping

The N-benzyloxycarbonyl-4-oxoproline ferr-butyl ester prepared from trans-4-hydroxy-L-proline was shown to be capable of a reductive amination with esters of α- or β-amino acids to the corresponding (45)-4-aminoderivatives. One of the resulting products, (45)-4-glycinoderivative, was easily cyclized after selective removal of the acid-labile protective group. There resulted bridge bicyclic synthons suitable for peptide synthesis: (2S,5S)-benzyloxycarbonyl-4-methoxycarbonylmethyl-3-oxo-1,4-diazabicyclo[2.2.1] heptane, (2S,5S)-1-(9-fluorenylmethoxycarbonyl-4-methoxycarbonyl-3-oxo-1,4- diazabicyclo[2.2.1 ]heptane, and (2S,5S)-1-(9-fluorenylmethoxycarbonyl-4-carboxymethyl-3-oxo-l,4-diazabicyclo[2. 2.1]heptane. Their possible use for the study of biologically significant conformations of bioactive proline-containing oligopeptides is discussed.