Highly stereoselective multigram scale synthesis of (3S,4S)-Statine and (3S,4S)-N-Benzylstatine - CY TECH : Sciences expérimentales Access content directly
Journal Articles Results in Chemistry Year : 2022

Highly stereoselective multigram scale synthesis of (3S,4S)-Statine and (3S,4S)-N-Benzylstatine

Synthèse multigramme hautement stéréosélective de (3S,4S)-Statine et de (3S,4S)-N-Benzylstatine

Abstract

Statins are essential naturally occurring β-hydroxy-γ-amino acids and (3S,4S)-Statine, derived from L-Leucine, is found in important aspartic proteases inhibitors like Pepstatin A. We developed a new synthesis of (3S,4S)- Statine based on the highly diastereoselective reduction of N,N-Boc/Benzyl protected β-ketoester intermediate. This Boc/Benzyl protection strategy gives access to either N-Fmoc or N-Benzyl protected (3S,4S)-Statine on multigram scale quantities.
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Dates and versions

hal-04098168 , version 1 (15-05-2023)

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Khoubaib Ben Haj Salah, Francesco Terzani, Marine Pietri, Chiara Zanato, Evelyne Chelain, et al.. Highly stereoselective multigram scale synthesis of (3S,4S)-Statine and (3S,4S)-N-Benzylstatine. Results in Chemistry, 2022, 4, pp.100333. ⟨10.1016/j.rechem.2022.100333⟩. ⟨hal-04098168⟩
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