Elaboration of a chiral 20‐crown‐6 from a glucofuranose derivative and its complex formation with alkali cations

P. Bakó, Laszló Fenichel, L. Tőke, Bruce E. Davison, Alpana Patel

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3 Citations (Scopus)

Abstract

The synthesis of bis‐(1,2‐O‐isopropylidene‐6‐O‐triphenylmethyl‐α‐D‐glucofuranosyl)‐20‐crown‐6 (1) and its complexing ability with alkali and ammonium cations are described. The crown ether 1 was synthesized in a stepwise manner via the “half‐crown” (2) using a blocking‐deblocking procedure, in which the 3,3′‐bridge was formed, followed after suitable manipulations, by formation of the 5,5′‐bridge. An unusual feature of the complexing ability of the crown ether is that, although potassium and ammonium ions most closely approach the size of the complexing cavity, it is the sodium ion which forms the most stable complex. Compound 1 does not show chiral recognition toward two alkylammonium salts.

Original languageEnglish
Pages (from-to)415-419
Number of pages5
JournalHeteroatom Chemistry
Volume5
Issue number4
DOIs
Publication statusPublished - 1994

ASJC Scopus subject areas

  • Chemistry(all)

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