217447-50-2

Upstream product

• 171514-06-0 methyl (3S,4S)-4-(O-t-butyldimethylsilyl)hydroxy-2,3,4,5-tetrahydropyridazine-3-carboxylate 
• 217447-41-1 methyl 5,5-dimethoxy-3-oxo-4-pentanoate 
• 217447-47-7 (R)-3-Hydroxy-5,5-dimethoxy-pentanoic acid methyl ester 
• 217447-49-9 Methyl (2R,3R)-5,5-dimethoxy-2-[N,N'-(dibenzylcarbonylhydrazino)]-3-hydroxypentanoate 
• 171514-04-8 methyl-(2S,3S)-2-(N,N-di-t-butyloxycarbonyl)hydrazino-3-hydroxyoct-5(E)-enoate 
• 163797-43-1 Methyl (E)-3-oxooct-5-enoate 
• 163955-02-0 methyl 3-(S)-3-hydroxy-5-(E)-octen-5-oate 
• 171514-05-9 methyl (2S,3S)-2-(N,N-di-t-butyloxycarbonyl)hydrazino-3-(O-t-butyldimethylsilyl)hydroxyoct-5(E)-enoate 

Relevant academic research and scientific papers

Synthesis of (3S,4S)-4-Hydroxy-2,3,4,5-Tetrahydropyridazine-3-Carboxylic Acid, Component of Luzopeptin A.

The enantioselective synthesis of (3S,4S)-4-hydroxy-2,3,4,5-tetrahydropyridazine-3-carboxylic acid 1 is described.The two stereogenic centers in anti relationship are obtained by sequential enantio and chemoselective hydrogenation of β-ketoester in presence of chiral ruthenium catalyst and diastereoselective amination of β-hydroxyester with di t-butylazodicarboxylate.

Rapid asymmetric synthesis of highly functionalized C5 chiral synthons. Practical preparation of trans-3 -hydroxy-D-proline

A stereocontrolled synthesis of (2R, 3R)-3-hydroxyproline 5 has been achieved in 33% overall yield from a prochiral β-ketoester : the methyl 5,5-dimethoxy-3-oxopentanoate 6. The key intermediate is the richly functionalized compound 4 which presented three different oxygenated groups and an anti relationship between the alcohol and the amine.