One-pot regioselective synthesis of 2(I),3(I)-O-(o-xylylene)-capped cyclomaltooligosaccharides: tailoring the topology and supramolecular properties of cyclodextrins.
The alpha,alpha'-dibromo-o-xylylene cap has been installed at the secondary hydroxyls of a single glucopyranosyl residue in cyclodextrins in one pot and with total regioselectivity; the resulting cyclic ether acts as a removable hinge, allowing selective elaboration of the secondary face and modulating both the self-association and the inclusion capabilities of the hosts.
Balbuena
Patricia
P
Departamento de Química Orgánica, Facultad de Química, Universidad de Sevilla, Apartado 553, Sevilla, E-41071, Spain.
Lesur
David
D
González Alvarez
M José
MJ
Mendicuti
Francisco
F
Mellet
Carmen Ortiz
CO
García Fernández
José M
JM
D003505:Cyclodextrins / Q000737:chemistry*; D009844:Oligosaccharides / Q000138:chemical synthesis*; D013237:Stereoisomerism; D014992:Xylenes / Q000737:chemistry*
D003505:Cyclodextrins; D009844:Oligosaccharides; D014992:Xylenes; C026114:2-xylene