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Regioselective Double Capping of Cyclodextrin Scaffolds
Author(s) -
GramageDoria Rafael,
RodriguezLucena David,
Armspach Dominique,
Egloff Coraline,
Jouffroy Matthieu,
Matt Dominique,
Toupet Loïc
Publication year - 2011
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201002541
Subject(s) - regioselectivity , reagent , chemistry , yield (engineering) , cyclodextrin , structural isomer , combinatorial chemistry , stereochemistry , crystallography , organic chemistry , materials science , catalysis , metallurgy
Four different regioselective double capping reactions were applied either to α‐ or β‐cyclodextrin (CD) scaffolds. The first, which relied on the use of a rigid, bulky dialkylating reagent containing two trityl‐like subunits, gave access to an A,B,D,E‐tetrafunctionalised β‐CD regioisomer in large scale reactions. Two further capping reactions, involving the dianions PhP 2− and S 2− , led to the synthesis of new C 1 ‐symmetrical β‐cyclodextrins in which pairs of neighbouring glucose units are linked by very short spacers. The last double capping reaction described allowed the high‐yield preparation of unprecedented α‐ and β‐cyclodextrins containing two sulfate handles. Proximal capping turned out to be favoured for each of the above difunctional reagents. The structural characterisation of the capped species was achieved by thorough NMR investigations as well as by single‐crystal X‐ray diffraction studies.