408535-10-4

Upstream product

• 18162-48-6 tert-butyldimethylsilyl chloride 
• 408535-03-5 (4S)-3-((3S)-6-hydroxy-3-phenylhexanoyl)-4-benzyl-1,3-oxazolidin-2-one 
• 128891-66-7 (4S)-4-benzyl-3-[(2E)-3-phenylprop-2-enoyl]-1,3-oxazolidin-2-one 
• 142078-08-8 (4S)-3-((3S)-3-phenylhex-5-enoyl)-4-benzyl-1,3-oxazolidin-2-one 

Downstream Products

• 408535-12-6 (2S,3R)-1-[(4S)-2-oxo-4-benzyl-1,3-oxazolidin-3-yl]-2-azido-6-hydroxy-3-phenylhexan-1-one 
• 408535-14-8 (4R,5S)-5-Azido-6-((S)-4-benzyl-2-oxo-oxazolidin-3-yl)-6-oxo-4-phenyl-hexanal 
• 408535-15-9 methyl (2S,3R)-3-phenylpiperidine-2-carboxylate 
• 90719-32-7 (S)-4-Benzyl-2-oxazolidinone 
• 408535-11-5 (2S,3R)-1-[(4S)-2-oxo-4-benzyl-1,3-oxazolidin-3-yl]-2-azido-3-phenyl-6-(1,1,2,2-tetramethyl-1-silapropoxy)hexan-1-one 

Relevant academic research and scientific papers

Enantioselective synthesis of Nα-Fmoc protected (2S,3R)-3-phenylpipecolic acid. A constrained phenylalanine analogue suitably protected for solid-phase peptide synthesis

Reported herein is the first enantioselective preparation of (2S,3R)-3-phenylpipecolic acid as a conformationally constrained phenylalanine analogue bearing Nα-protection suitable for solid-phase peptide synthesis. Stereochemistries at both the 2- and 3-positions are derived inductively from a single chiral center provided by the commercially available Evans chiral auxiliary, (4S)-4-benzyl-1,3-oxazolidin-2-one. By constraining φ and χ1 torsion angles, this novel amino acid analogue can serve as a useful tool for the induction of defined geometry in phenylalanine-containing peptides.