Stereoselective Synthesis of Hydroxyethylene Dipeptide Isostere from Sugar
- 1 June 1996
- journal article
- research article
- Published by Taylor & Francis in Synthetic Communications
- Vol. 26 (11) , 2045-2056
- https://doi.org/10.1080/00397919608003563
Abstract
Regioselective opening of the aziridine ring in the carbohydrate-based precursor led to the stereoselective synthesis of N-Boc-O-benzyl-(4S,5S)-5-amino-4-hydroxy-6-phenylhexanoic acid methyl ester, the hydroxyethylene dipeptide isostere moiety of potent HIV-1 protease inhibitor.Keywords
This publication has 16 references indexed in Scilit:
- A simple strategy for the synthesis of hydroxyethylene dipeptide isostere from D-glucoseTetrahedron, 1995
- Peptidomimetics—Tailored Enzyme InhibitorsAngewandte Chemie International Edition in English, 1994
- STRUCTURE-BASED INHIBITORS OF HIV-1 PROTEASEAnnual Review of Biochemistry, 1993
- A new enantioselective synthesis of (4S, 5S)-5-(N-Boc)-amino-6-cyclohexyl-4-hydroxy-hexanoic acid lactone, a hydroxyethylene dipeptide isostere precursorTetrahedron Letters, 1991
- An efficient synthesis of hydroxyethylene dipeptide isosteres: the core unit of potent HIV-1 protease inhibitorsThe Journal of Organic Chemistry, 1991
- HIV protease: a novel chemotherapeutic target for AIDSJournal of Medicinal Chemistry, 1991
- Stereoselective synthesis of N-Boc-O-benzyl-(4S,5S)-5-amino-4-hydroxy-6-phenylhexanoic acid, the hydroxyethylene isosteric moiety of potent HIV-1 protease inhibitorTetrahedron Letters, 1991
- Synthesis of renin inhibitors possessing hydroxyethylene isostere residue from 3,4,6-tri-O-acetyl-D-qlucal via lactone precursorTetrahedron, 1991
- Nucleophilic ring opening of C2-symmetric aziridines. Synthetic equivalents for the β-cation of aspartic acidTetrahedron Letters, 1990
- Synthesis of (4s,5r)-(+)-factor, a proposed autoregulator of anthracycline biosynthesisTetrahedron, 1984