4-(tert-Butyldimethylsilyloxy)benzylidene acetal: A novel benzylidene-type protecting group for 1,2-diols

Yosuke Kaburagi, Hiroyuki Osajima, Kousei Shimada, Hidetoshi Tokuyama, Tohru Fukuyama

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

A novel 1,2-diol-protecting group, p-silyloxybenzylidene group, has been developed. In addition to the stepwise deprotection conditions including desilylation and the subsequent acidic hydrolysis of the p-hydroxybenzylidene group in AcOH-THF-H2O, we have established the one-pot deprotection under basic conditions [K2CO3 (5equiv), NH 2OH·HCl (5equiv), and CsF (1equiv) in MeOH-H2O].

Original languageEnglish
Pages (from-to)3817-3821
Number of pages5
JournalTetrahedron Letters
Volume45
Issue number19
DOIs
Publication statusPublished - 2004 May 3
Externally publishedYes

Keywords

  • Benzylidene acetal
  • Deprotection under basic conditions
  • Diol
  • Hydroxylamine
  • Protecting group

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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