Structure of a peptide surrogate, tert-butoxycarbonylalanyl-ψ(CH2S)-phenylalanine [Boc-Ala-ψ(CH2S)-Phe-OH]

“Carba” peptide bond surrogates: synthes

“Carba” peptide bond surrogates: synthesis of Boc-L-Leu-…(CH2-CH2)-L-Phe-OH and Boc-LLeu-ψ-(CH2-CH2)-D-Phe-OH through a horner-emmons reaction.

✍ Marc Rodriguez; Annie Heitz; Jean Martinez 📂 Article 📅 1990 🏛 Elsevier Science 🌐 French ⚖ 265 KB

## Abstra A synthesis of Boc-L-Leu-\r(CHz-CHz&Phe-OH and Boc-~-L~u-u~(CH~-CH~)-Q-Phe-OH from Boc-ghomo-L-leucinal, through a Horner-Emmons reaction with ethyl 2-(diethylphosphono)-3-phenylpropionate is described. Intermediate cyclisation into lactames (3S,6R)-3-benzyl6-isobutyl-piperidin-2-one and