637337-46-3

Basic information

• Product Name: (R)-3-(3-{4-[(tert-butyldiphenylsilyl)oxy]phenyl}-1-oxopropyl)-4-isopropyl-5,5-diphenyloxazolidin-2-one
• Synonyms: (R)-3-(3-{4-[(tert-butyldiphenylsilyl)oxy]phenyl}-1-oxopropyl)-4-isopropyl-5,5-diphenyloxazolidin-2-one
• CAS NO: 637337-46-3
• Molecular Weight: 667.92
• Mol File: 637337-46-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (R)-3-(3-{4-[(tert-butyldiphenylsilyl)oxy]phenyl}-1-oxopropyl)-4-isopropyl-5,5-diphenyloxazolidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-3-(3-{4-[(tert-butyldiphenylsilyl)oxy]phenyl}-1-oxopropyl)-4-isopropyl-5,5-diphenyloxazolidin-2-one(637337-46-3)
• EPA Substance Registry System: (R)-3-(3-{4-[(tert-butyldiphenylsilyl)oxy]phenyl}-1-oxopropyl)-4-isopropyl-5,5-diphenyloxazolidin-2-one(637337-46-3)

Safety Data

• Hazardous Substances Data: 637337-46-3(Hazardous Substances Data)

Upstream product

• 58479-61-1 tert-butylchlorodiphenylsilane 
• 501-97-3 4-hydroxyphenylpropionic acid 
• 191090-32-1 (R)-4-(1-methylethyl)-5,5-diphenyl-1,3-oxazolidin-2-one 
• 671233-59-3 3-{4-[(tert-butyldiphenylsilyl)oxy]phenyl}propanoic acid 

Downstream Products

• 637337-62-3 (R)-3-[(S)-2-{[(benzyloxy)carbonyl]amino}methyl-3-{4-[(tert-butyl)diphenylsilyl]oxy}phenyl-1-oxopropyl]-4-isopropyl-5,5-diphenyloxazolidin-2-one 
• 671233-61-7 2-aminomethyl-3-(4-tert-butoxy-phenyl)-propionic acid 
• 637337-77-0 (S)-2-{[(benzyloxy)carbonyl]amino}methyl-3-[4-(tert-butoxy)phenyl]propanoic acid 
• 671233-53-7 (R)-3-[(S)-2-{[(benzyloxy)carbonyl]amino}methyl-3-(4-hydroxyphenyl)-1-oxopropyl]-4-isopropyl-5,5-diphenyloxazolidin-2-one 
• 671233-54-8 (R)-3-[(S)-2-{[(benzyloxy)carbonyl]amino}methyl-3-[4-(tert-butoxy)phenyl]-1-oxopropyl]-4-isopropyl-5,5-diphenyloxazolidin-2-one 

Relevant articles and documents

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.