On the basis for regioselective oxidation within a tetragalloylpyranose substrate

Ken S. Feldman, Kendra L. Hunter

Research output: Contribution to journalArticlepeer-review

3 Scopus citations

Abstract

Lead (IV)-mediated oxidation of a benzyl 2,3,4,6- tetragalloylglucopyranoside leads only to coupling at the O(4)/O(6) galloyls. Competitive oxidation experiments with a series of positionally distinct phenolic galloyl analogs furnishes evidence that this unexpected regioselectivity stems from preferential oxidation at the O(6) galloyl ring. Companion studies with electronically dissimilar analogs provide support for a through-space component to O(6) galloyl oxidation selectivity in addition to steric and inductive influences.

Original languageEnglish (US)
Pages (from-to)8943-8946
Number of pages4
JournalTetrahedron Letters
Volume39
Issue number49
DOIs
StatePublished - Dec 3 1998

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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