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Hydroxy Group Acidities of Partially Protected Glycopyranosides
Author(s) -
Matwiejuk Martin,
Thiem Joachim
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201101708
Subject(s) - chemistry , intramolecular force , solvation , hydrogen bond , carbohydrate , group (periodic table) , medicinal chemistry , organic chemistry , stereochemistry , molecule
Abstract A comprehensive acidity study of carbohydrate hydroxy groups has been carried out. Relative acidities ( K e ) were determined spectrophotometrically for partially methylated methyl α‐ D ‐glycopyranosides. Apparently, the acidity is strongly affected by intramolecular hydrogen bonding as well as stereochemistry and solvation. By comparison with p K e and p K a values of aliphatic alcohols and polyols the first estimation of the p K a values for partially protected glycopyranosides was obtained. These findings contribute to the understanding of the relative reactivities of carbohydrate hydroxy groups.