(1S)-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-hydroxyethylammonium benzoate, a versatile building block for chiral 2-aminoalkanols:: Concise synthesis and application to nelfinavir, a potent HIV-protease inhibitor

被引:55
作者
Inaba, T [1 ]
Yamada, Y [1 ]
Abe, H [1 ]
Sagawa, S [1 ]
Cho, H [1 ]
机构
[1] Japan Tobacco Inc, Cent Pharmaceut Res Inst, Takatsuki, Osaka 5691125, Japan
关键词
D O I
10.1021/jo991793e
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
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-hydroxyethammonium benzoate (la), was described. 1 (1a and its enantiomer 1b) acted as four stereoisomers of optically active 2-amino-1,3,4-butanetriol. The versatility of I 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.
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页码:1623 / 1628
页数:6
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