89625-39-8

Upstream product

• 108-24-7 acetic anhydride 
• 13504-85-3 (2S,4R)-1-(benzyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid 
• 501-53-1 benzyl chloroformate 
• 51-35-4 4R-4-hydroxyproline 

Downstream Products

• 224321-02-2 (2S,4R)-4-Acetoxy-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester 
• 89625-49-0 C₁₅H₁₉NO₅ 
• 72289-52-2 (2S,4R)-4-hydroxy-1-phenylmethoxycarbonylpyrrolidine-2-carboxylic acid tert-butyl ester 
• 89625-40-1 (S)-4-Acetoxy-2-[2-bromo-4-methoxy-5-(toluene-4-sulfonyloxy)-phenylcarbamoyl]-pyrrolidine-1-carboxylic acid benzyl ester 

Relevant academic research and scientific papers

Metal-free, direct conversion of α-amino acids into α-keto γ-amino esters for the synthesis of α,γ-peptides

An efficient, metal-free synthesis of unusual α-keto γ-amino esters from α-amino acids is achieved by a radical scission-oxidation-addition of silyloxy acrylates procedure, where no purification of the reaction intermediates is needed. This protocol can be applied to the selective modification of the C-terminal position in peptides to give α,γ-hybrids.

Aminal-pyrrolidine organocatalysts - Highly efficient and modular catalysts for α-functionalization of carbonyl compounds

The substitution of the 4-position of hydroxyproline by a phenol group, together with an aminal on the 2-position, gave a synergistic effect leading to two powerful complementary organocatalysts. They show excellent enantiocontrol in the α-functionalization of a wide range of linear/ branched aldehydes and ketones, including Michael additions to ethenediyl disulfones or nitrostyrene and α-amination. We obtained ees up to 98.5 % with low catalyst loadings (down to 1 mol-%). As a proof of efficiency, TOFs of up to 1000 h-1 could be obtained.

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.