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Synthesis of Per(5‐carboxy‐5‐dehydroxymethyl)‐α‐ and β‐Cyclodextrins −Self‐Assembly of the Per(2,3‐di‐ O ‐methyl)‐Protected Homologues into Highly Stable Dimers, Driven by Multiple Hydrogen Bonds
Author(s) -
Kraus Tomáš,
Buděšínský Miloš,
Závada Jirˇí
Publication year - 2000
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 - 10.1002/1099-0690(200009)2000:18<3133::aid-ejoc3133>3.0.co;2-p
Subject(s) - chemistry , vapor pressure osmometry , hydrogen bond , hydrolysis , alkaline hydrolysis , medicinal chemistry , self assembly , osmometer , polymer chemistry , hydrogen , cyclodextrin , organic chemistry , stereochemistry , vapor pressure , molecule
Abstract Per(2,3‐di‐ O ‐methyl)‐ and per(2,3‐di‐ O ‐acetyl)‐ α‐ and β‐cyclodextrins were smoothly converted into the corresponding per(5‐carboxy‐5‐dehydroxymethyl) derivatives 2a , 2b , 4a and 4b by TEMPO‐mediated oxidation. Alkaline hydrolysis of the per(2,3‐di‐ O ‐acetyl)‐substituted polycarboxylic acids affords the naked per(5‐carboxy‐5‐dehydroxymethyl)cyclodextrins 5a and 5b in quantitative yields. Self‐assembly, driven by hydrogen bonds, of the per(2,3‐di‐ O ‐methyl)‐protected homologues 2a and 2b affords highly stable dimers, as evidenced by vapour‐pressure osmometry in 1,2‐dichloroethane solution.