TY - JOUR
T1 - (1S)-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-hydroxyethylammonium benzoate, a versatile building block for chiral 2-aminoalkanols
T2 - Concise synthesis and application to nelfinavir, a potent HIV-protease inhibitor
AU - Inaba, Takashi
AU - Yamada, Yasuki
AU - Abe, Hiroyuki
AU - Sagawa, Shoichi
AU - Cho, Hidetsura
PY - 2000/3/24
Y1 - 2000/3/24
N2 - 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- hydroxyethylammonium benzoate (1a), was described. 1 (1a and its enantiomener 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.
AB - 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- hydroxyethylammonium benzoate (1a), was described. 1 (1a and its enantiomener 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.
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U2 - 10.1021/jo991793e
DO - 10.1021/jo991793e
M3 - Article
C2 - 10750488
AN - SCOPUS:0034708584
VL - 65
SP - 1623
EP - 1628
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 6
ER -
