(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

Takashi Inaba, Yasuki Yamada, Hiroyuki Abe, Shoichi Sagawa, Hidetsura Cho

Research output: Contribution to journalArticlepeer-review

52 Citations (Scopus)

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- 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.

Original languageEnglish
Pages (from-to)1623-1628
Number of pages6
JournalJournal of Organic Chemistry
Volume65
Issue number6
DOIs
Publication statusPublished - 2000 Mar 24

ASJC Scopus subject areas

  • Organic Chemistry

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