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Synthesis of chiral N-protected β-amino alcohols by the use of UNCAs

✍ Scribed by Jean-Alain Fehrentz; Jean-Christophe Califano; Muriel Amblard; Albert Loffet; Jean Martinez

Publisher
Elsevier Science
Year
1994
Tongue
French
Weight
222 KB
Volume
35
Category
Article
ISSN
0040-4039

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✦ Synopsis

A facile synthesis of a wide variety of N-protected p-amino akobol derivatives under mild conditions is described. N-umtbane proceded amino acid N-carboxyanhydrides (UNCAs) were used as starting ma&al and reduced into the correspooding akohols with the appropriate hydride, sodium borobydride. The reaction is simple, unexpensive, e&ly scaled up, and pmceeds witbout observable mcemization. N-protected pamino alcohols are of great interest in the synthesis of pcptidc bond surrogates because they are key intermediates for the obtention of a-amino aldehydes by oxydationl which are potent inhibitors of proteases or for the preparation of stereochemically

📜 SIMILAR VOLUMES

A facile synthesis of chiral N-protected
A facile synthesis of chiral N-protected β-amino alcohols.
✍ Marc Rodriguez; Muriel Llinares; Sylvie Doulut; Annie Heitz; Jean Martinez 📂 Article 📅 1991 🏛 Elsevier Science 🌐 French ⚖ 211 KB

Chiral N-protected p-amino alcohols are easily obtained by NaB& reduction of mixed anhydndes of N-protected a-ammo acids m an organic/aqueous medium. The alcohols obtamed from side chain or main chain reduction of N-protected asparhc acid are converted in good yields into lactones.