Regioselective difunctionalization of cyclodextrins.

TY - JOUR

T1 - Regioselective difunctionalization of cyclodextrins.

AU - Petrillo, Marta

AU - Marinescu-Pedersen, Lavinia G

AU - Bols, Mikael

PY - 2011/4

Y1 - 2011/4

N2 - An efficient route for selective functionalization of cyclodextrin diols (2A-F,3A-F,6B,C,E,F-hexadeca-O-benzyl-α- cyclodextrin or 2A-G,3A-G,6B,C,E-G-nonadeca-O- benzyl-β-cyclodextrin) is reviewed here. It has been reported that these diols can be transformed into 6A,6D-cyclic sulfites, which can be oxidized to 6A,6D-cyclic sulfates in good yields. The latter can be regioselectively opened by nucleophilic attack from one side of the bridge. This behavior allowed the synthesis of various potential artificial glycosidases and phosphorylases in which one moiety would work as the catalyst, the other one would be investigated as assisting group. The synthesis of new hetero-functionalized cyclodextrins is presented here.

AB - An efficient route for selective functionalization of cyclodextrin diols (2A-F,3A-F,6B,C,E,F-hexadeca-O-benzyl-α- cyclodextrin or 2A-G,3A-G,6B,C,E-G-nonadeca-O- benzyl-β-cyclodextrin) is reviewed here. It has been reported that these diols can be transformed into 6A,6D-cyclic sulfites, which can be oxidized to 6A,6D-cyclic sulfates in good yields. The latter can be regioselectively opened by nucleophilic attack from one side of the bridge. This behavior allowed the synthesis of various potential artificial glycosidases and phosphorylases in which one moiety would work as the catalyst, the other one would be investigated as assisting group. The synthesis of new hetero-functionalized cyclodextrins is presented here.

M3 - Journal article

SN - 1388-3127

SP - 425

EP - 431

JO - Journal of Inclusion Phenomena and Macrocyclic Chemistry

JF - Journal of Inclusion Phenomena and Macrocyclic Chemistry

ER -