Practical synthesis of four stereoisomers of 6-(t-butyldiphenylsiloxy)- 3,5-dimethyl-1-(triphenylmethoxy)hexane-2,4-diol via dithiane coupling with oxirane

Mitsuaki Ide, Keiji Tsunashima, Masaya Nakata

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

The anion derived from 2-substituted 1,3-dithiane derivative (S)-2-[2- (t-butyldiphenylsiloxy)-1-methylethyl]-1-3-dithiane, with n-BuLi at room temperature (r.t.) in THF was subjected to coupling with 2,3-disubstituted oxirane, (2S,3S), or (2S,3R)-2,3-epoxy-1-(triphenylmethoxy)butane, at r.t., giving the coupling products in satisfactory yield. These coupling products were subjected to de-dithioacetalization, and the resulting carbonyl compounds were stereoselectively reduced to afford four stereoisomers of 6- (t-butyldiphenylsiloxy)-3,5-dimethyl-1-(triphenylmethoxy)hexane-2,4-diol.

Original languageEnglish
Pages (from-to)2501-2507
Number of pages7
JournalBulletin of the Chemical Society of Japan
Volume72
Issue number11
DOIs
Publication statusPublished - 1999 Nov

ASJC Scopus subject areas

  • Chemistry(all)

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