84969-25-5

Upstream product

• 501-53-1 benzyl chloroformate 
• 13504-85-3 (2S,4R)-1-(benzyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid 
• 100-39-0 benzyl bromide 
• 64187-47-9 1-benzyloxycarbonyl-4-keto-L-proline 
• 51-35-4 4R-4-hydroxyproline 
• 13500-53-3 N-benzyloxycarbonyl-(2S,4R)-4-hydroxyproline benzyl ester 

Downstream Products

• 1316105-42-6 C₂₄H₂₆N₂O₄ 
• 903518-05-8 (2S)-4-cyanomethyl-2,5-dihydropyrrole-1,2-dicarboxylic acid dibenzyl ester 
• 903518-04-7 (2S)-4-cyanomethylenepyrrolidine-1,2-dicarboxylic acid dibenzyl ester 
• 119595-95-8 (2S,4S)-4-(cyanomethyl)proline 
• 119595-96-9 (2S,4R)-4-(cyanomethyl)proline 
• 903518-07-0 (2S,4S)-4-(2-tert-butoxycarbonylaminoethyl)pyrrolidine-1,2-dicarboxylic acid dibenzyl ester 

Relevant academic research and scientific papers

Preparation method of intermediate

The invention relates to a preparation method of an intermediate, and belongs to the field of medicinal chemistry. The preparation method comprises at least one reaction step of an addition elimination reaction, a cyclization reaction, a reduction reaction, a decarboxylation reaction and a hydrogenation reaction. According to the method disclosed by the invention, the target intermediate with a single configuration can be simply and conveniently obtained, chiral resolution is effectively avoided, the yield is improved, the cost is reduced, and industrial production is facilitated.

Synthesis of novel haptens and conjugates for antibody production against kainoid family

Amnesic shellfish poisoning (ASP) is caused by consumption of contaminated seafood that has accumulated kainic acid or kainoid analogues such as domoic acid. Among the different ASP bioassays, immunoassays are an attractive alternative to the in vivo mouse bioassay. Herein, we report the synthesis and bioconjugation of two new haptens for the generation of a specific antibody against members of the kainoid family. Georg Thieme Verlag Stuttgart.

Synthesis of conformationally constrained lysine analogues

The synthesis of two conformationally constrained lysine analogues is reported. The synthesis of the novel analogue 1 based on the 3-aza-bicyclo[3.1.0]hexane system is accomplished from the known tricycle 3 in eight steps. The synthesis of the analogue 2 is accomplished in eight steps from 4-hydroxy proline. Both analogues are synthesized appropriately protected for Fmoc/Boc solid-phase peptide synthesis.

Stereoselective synthesis of novel chimerical amino acids via a photochemical key step

The synthesis of novel chimerical amino acid derivatives 6-8 bearing the 6-azatricyclo[3.3.1.033,7]nonane (methanotropane) skeleton is described. Starting with one chirality centre in L-4-oxoprolines 2 we succeeded in the fully stereoselective introduction of four new chirality centres. The key step of our synthetic route is a photochemical cyclization of phenyl ketones, whose stereoselectivity has been explained by the different stability of the triplet biradical conformers.

Method for the preparation of N-substituted 4-ketoproline derivatives

Method for the preparation of N-protected 4-ketoproline derivatives of formula I STR1 by oxidation of the corresponding N-protected 4-hydroxyproline derivatives of STR2 using the system TEMPO (2,2,6,6-tetramethylpiperidinyl oxy free radical)/NaOCl.