Preferential Recognition and Extraction to Pentoses over Hexoses by a D6 h-Symmetrical Ethynylphenol Macrocycle with Six Inner Phenolic Hydroxy Groups

Tomoya Hayashi, Yuki Ohishi*, Hajime Abe, Masahiko Inouye*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

12 Scopus citations

Abstract

A macrocycle consisting of six ethynylphenol units was developed as a host architecture for saccharides. The rigid framework of the macrocycle suppressed the intramolecular hydrogen-bonding between adjacent phenolic hydroxy groups and recognized saccharides by intermolecular hydrogen-bonding within the hole. The well-defined hydrogen-bonding sites enabled the size-selective guest recognition and showed preference to pentoses over hexoses.

Original languageEnglish
Pages (from-to)1927-1934
Number of pages8
JournalJournal of Organic Chemistry
Volume85
Issue number4
DOIs
StatePublished - 2020/02/21

ASJC Scopus subject areas

  • Organic Chemistry

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