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(1S)-1-[(4R)-2,2-dimethyl-1,3-dioxolan+-4-yl][-2-hydroxyethylamm onium benzoate, a versatile building block for chiral 2-aminoalkanols: concise synthesis and application to nelfinavir, a potent HIV-protease inhibitor.
- Source :
-
The Journal of organic chemistry [J Org Chem] 2000 Mar 24; Vol. 65 (6), pp. 1623-8. - Publication Year :
- 2000
-
Abstract
- A concise synthesis of a versatile chiral C4 building block for 2-aminoalkanols, (1S)-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-hydroxyethylammo nium benzoate (1a), was described. 1 (1a and its enantiomer 1b) acted as four stereoisomers of optically active 2-amino-1,3,4-butanetriol. The versatility of 1 was demonstrated by its application to the practical synthesis of nelfinavir (2), a potent HIV-protease inhibitor, as well as by the stereospecific synthesis of three diastereomers of 2.
Details
- Language :
- English
- ISSN :
- 0022-3263
- Volume :
- 65
- Issue :
- 6
- Database :
- MEDLINE
- Journal :
- The Journal of organic chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 10750488
- Full Text :
- https://doi.org/10.1021/jo991793e