128359-96-6

Upstream product

• 81927-55-1 O-benzyl 2,2,2-trichloroacetimidate 
• 128359-95-5 (2S,4S)-Methyl 4-acetoxy-1-<<2-(trimethylsilyl)ethyl>oxycarbonyl>pyrrolidine-2-carboxylate 
• 128360-00-9 (2S,4R)-Methyl 4-hydroxy-1-<<2-(trimethylsilyl)ethyl>oxycarbonyl>pyrrolidine-2-carboxylate 
• 40216-83-9 L-4-hydroxyproline methyl ester hydrochloride 
• 13504-85-3 (2S,4R)-1-(benzyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid 
• 51-35-4 4R-4-hydroxyproline 
• 13500-53-3 N-benzyloxycarbonyl-(2S,4R)-4-hydroxyproline benzyl ester 
• 64187-48-0 methyl (2S,4R)-1-benzyloxycarbonyl-4-hydroxypyrrolidine-2-carboxylate 
• 64-19-7 acetic acid 

Relevant academic research and scientific papers

Electrochemical Oxidation of Proline Derivatives: Total Syntheses of Bulgecinine and Bulgecin C

The influence of structure on the efficiency of the electrochemical C-5 oxidation of (2S,4S)-hydroxyproline carbamate esters is presented.Optimum methoxylation was observed with (2S,4S)-4-acetoxy-1,2-pyrrolidine-dicarboxylic acid 2-methyl 1-(2-(trimethylsilyl)ethyl) ester (19).The corresponding C-5 methoxy derivative 20 was converted into bulgecinine (4) via a stereospecific radical homologation to incorporate the C-5 hydroxymethyl substituent.Bulgecin C (1c) was prepared via a β-stereoselective glycosidation reaction using a 2-azido-2-deoxy-α-D-glucopyranosyl trichloroacetimidate derivative, regiospecific C-4' sulfation, and deprotection.