(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.
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.
Inaba
T
T
Central Pharmaceutical Research Institute, Japan Tobacco, Inc, Osaka, Japan.
Yamada
Y
Y
Abe
H
H
Sagawa
S
S
Cho
H
H
D000605:Amino Alcohols / Q000138:chemical synthesis / Q000737:chemistry*; D017320:HIV Protease Inhibitors / Q000737:chemistry; D019888:Nelfinavir / Q000737:chemistry; D013237:Stereoisomerism
D000605:Amino Alcohols; D017320:HIV Protease Inhibitors; D019888:Nelfinavir