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A Straightforward Synthesis of 1‐Adamantylmethyl Glycosides, and Their Binding to Cyclodextrins
Author(s) -
Charbonnier Florence,
Penadés Soledad
Publication year - 2004
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.200400141
Subject(s) - chemistry , pyranose , moiety , monosaccharide , glycoside , stereochemistry , cyclodextrin , nuclear magnetic resonance spectroscopy , organic chemistry
A single‐step synthesis of 1‐adamantylmethyl α‐ and β‐glycosides starting from commercially available peracetylated monosaccharides is reported. The α‐ and β‐glucopyranosides 1a and 1b bind to β‐cyclodextrin with association constants in the order of 10 5 M −1 , as determined by 1 H NMR spectroscopy. The carbohydrate moiety contributes to the binding depending on the pyranose stereochemistry. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)