637337-63-4

Upstream product

• 94471-35-9 benzyl N-(methoxymethyl) carbamate 
• 637337-47-4 (4R)-3-[(3S)-3-methylpentanoyl]-5,5-diphenyl-4-(propan-2-yl)-1,3-oxazolidin-2-one 
• 1730-92-3 (3S)-methylvaleric acid 
• 191090-32-1 (R)-4-(1-methylethyl)-5,5-diphenyl-1,3-oxazolidin-2-one 

Downstream Products

• 637337-71-4 (2S,3S)-2-({[(benzyloxy)carbonyl]amino}methyl)-3-methylpentanoic acid 

Relevant academic research and scientific papers

MASP INHIBITORY COMPOUNDS AND USES THEREOF

The present invention relates to novel Mannose-binding lectin (MBL)-associated serine protease (MASP) inhibitory compounds, as well as analogues and derivatives thereof, to processes for the preparation thereof, to the use thereof alone or in combinations for treatment and/or prevention of diseases and to the use thereof for production of medicaments for treatment and/or prevention of diseases, especially for treatment and/or prevention of renal and cardiovascular disorders and of ischemia reperfusion injuries.

Preparation of (S,S)-Fmoc-β2hIle-OH, (S)-Fmoc-β 2hMet-OH, and (S)-Fmoc-β2hTyr(tBu)-OH for Solid-Phase Syntheses of β2- and β2/β 3-Peptides

The preparation of three new N-Fmoc-protected (Fmoc=[(9H-fluoren-9-yl)methoxy]carbonyl) β2-homoamino acids with proteinogenic side chains (from Ile, Tyr, and Met) is described, the key step being a diastereoselective amidomethylation of the corresponding Ti-enolates of 3-acyl-4-isopropyl-5,5-diphenyloxazolidin-2-ones with CbzNHCH2OMe/TiCl4 (Cbz=(benzyloxy)carbonyl) in yields of 60-70% and with diastereoselectivities of > 90%. Removal of the chiral auxiliary with LiOH or NaOH gives the N-Cbz-protected β-amino acids, which were subjected to an N-Cbz/N-Fmoc (Fmoc=[(9H-fluoren-9-yl)methoxy]carbonyl) protective-group exchange. The method is suitable for large-scale preparation of Fmoc-β2hXaa-OH for solid-phase syntheses of β-peptides. The Fmoc-amino acids and all compounds leading to them have been fully characterized by melting points, optical rotations, IR, 1H- and 13C-NMR, and mass spectra, as well as by elemental analyses.

Enantioselective preparation of 2-aminomethyl carboxylic acid derivatives: Solving the β2-amino acid problem with the chiral auxiliary 4-isopropyl-5,5-diphenyloxazolidin-2-one (DIOZ)

Multigram amounts of suitably protected β2-amino acids with 17 of the 20 proteinogenic side chains are prepared by diastereoselective reactions of Li, B, or Ti enolates of the corresponding 3-acyl-4-isopropyl-5,5-diphenyloxazolidin-2-ones (acyl-DIOZ; 1) with appropriate electrophiles (amidomethylation, hydroxyalkylation, (benzyloxycarbonyl)methylation) in yields of 55-90% and with diastereoselectivities of 80 to > 97% (Scheme). The primary products 2-8 thus obtained are converted to protected β2-amino acids by standard procedures (Table 1). Many of the DIOZ derivatives are highly crystalline compounds (31 X-ray crystal structures in Table 2). The chiral auxiliary DIOZ, readily prepared in either enantiomeric form, is recovered with high yield.