155099-11-9

Upstream product

• 160002-06-2 (S)-tert-butyl 3-oxo-1-phenylhex-5-en-2-ylcarbamate 
• 1034089-11-6 tert-butyl (1S)-1-benzyl-2-hydroxypent-4-enylcarbamate 
• 87694-53-9 Boc-Phe-OH N,O-dimethyl hydroxamate 
• 181781-42-0 (1S,2E)-(1-benzyl-penta-2,4-dienyl)-carbamic acid tert-butyl ester 

Downstream Products

• 124266-92-8 Methyl (3R,4R,5S)-5-<(tert-butoxycarbonyl)amino>-3,4-epoxy-6-phenylhexanoate 
• 134210-24-5 methyl (4S,5S,2E)-5-amino-N-<(tert-butyloxy)carbonyl>-4-hydroxy-6-phenyl-2-hexanoate 
• 118457-05-9 Methyl (S)-5-<(tert-butoxycarbonyl)amino>-6-phenyl-(E)-3-hexenoate 
• 82042-48-6 (S)-5-<(tert-Butoxycarbonyl)amino>-6-phenyl-(E)-3-hexenoic acid 

Relevant academic research and scientific papers

Novel synthesis of a Phe-Gly E-alkene dipeptide isostere

A new strategy for the synthesis of Boc-Pheψ(E-CH=CH)Gly-OH (11) is described. The double bond is generated employing a β elimination of the mesyloxy group of 6. This elimination proves to be the key step within the synthesis. Different products are obtained dependent on the base as well as on the reaction conditions. Employing KOtBu leads to E-(5S)-(t-Butyloxycarbonylamino)-6-phenyl-1,3-hexadiene 7 whereas NaOMe causes a γ elimination resulting the aziridine 9. Diene 7 is converted into the corresponding Pheψ(E-CH=CH)Gly isostere by subsequent hydroboration and Jones oxidation.

Stereoselective Epoxidation of Phe-Gly and Phe-Phe Vinyl Isosteres

Novel Phe-Gly and Phe-Phe isosteres have been synthesized.Vinylic isosteres of Phe-Gly and Phe-Phe were prepared by facile Julia reactions, and the resulting stereoisomers were isolated and epoxidized (m-chloroperbenzoic acid).Observed stereoselectivities