Selective discrimination of cyclodextrin diols using cyclic sulfates.
A method for selective monofunctionalition of readily available cyclodextrin diols (2(A-F),3(A-F),6(B,C,E,F)-hexadeca-O-benzyl-alpha-cyclodextrin and 2(A-G),3(A-G),6(B,C,E-G)-nonadeca-O-benzyl-beta-cyclodextrin) by regioselective nucleophilic opening of their cyclic sulfates is presented. Although the A and D products are nonequivalent in beta-cyclodextrin, only the A product is formed.
Petrillo
Marta
M
Department of Chemistry and Nanoscience Center, University of Copenhagen, Copenhagen DK-2100, Denmark.
Marinescu
Lavinia
L
Rousseau
Cyril
C
Bols
Mikael
M
D000438:Alcohols / Q000737:chemistry; D001386:Azides / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D013431:Sulfates / Q000737:chemistry*; D047392:beta-Cyclodextrins / Q000138:chemical synthesis* / Q000737:chemistry
D000438:Alcohols; D001386:Azides; D013431:Sulfates; D047392:beta-Cyclodextrins; C031215:betadex