(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

研究成果: Article査読

55 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)1623-1628
ページ数6
ジャーナルJournal of Organic Chemistry
65
6
DOI
出版ステータスPublished - 2000 3 24

ASJC Scopus subject areas

  • 有機化学

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「(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」の研究トピックを掘り下げます。これらがまとまってユニークなフィンガープリントを構成します。

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