Synthesis of Cycloheptaamylose 2-, 3-, and 6-Phosphoric Acids, and a Comparative Study of Their Effectiveness as General Acid or General Base Catalysts with Bound Substrates1

Brock Siegel, Abraham Pinter, Ronald Breslow

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49 Scopus citations

Abstract

The title compounds were prepared and examined as catalysts for the hydrolysis of p-nitrophenyl tetrahydropyranyl ether at low pH and the exchange of p-tert-butylphenacyl alcohol tritiated in the methylene group at high pH. All three isomers, as the phosphate dianions, were effective catalysts for the latter reaction, in which the functional group assists enolization of the bound ketone. Only the 3-phosphoric acid isomer showed net catalysis of the former reaction, bound substrate being hydrolyzed with the assistance of a monoanion phosphoric acid group.

Original languageEnglish (US)
Pages (from-to)2309-2312
Number of pages4
JournalJournal of the American Chemical Society
Volume99
Issue number7
DOIs
StatePublished - 1977
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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