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Synthesis of monosubstituted derivatives of cyclodextrins
Řezanka, Michal
1 Synthesis of monosubstituted derivatives of cyclodextrins Abstract This thesis is focused on a preparation of a set of exactly defined monosubstituted derivatives of -CD for subsequent utilization in organic synthesis. Cinnamyl or allyl group is very suitable for the preparation of monosubstituted derivatives of CD, because these groups contain nonaromatic double bond, which can be widely modified. Peracetylated 2I -O-, 3I -O-, and 6I -O-allyl and 2I -O- and 3I -O-cinnamyl derivatives of -CD mentioned in this thesis were prepared in yields 3.7 - 13 %. Position of allyl and cinnamyl group was determined by 2D NMR techniques. Possibility of derivatization of allyl and cinnamyl derivatives was exemplified by transformation of peracetylated 2I -O-, and 6I -O-allyl and 3I -O-cinanmyl derivatives to peracetylated 2I -O-, 3I -O-, and 6I -O-formylmethyl derivatives via reductive ozonolysis. These aldehydes were oxidized by Jones reagent to 2I -O-, 3I -O-, and 6I -O-carboxymethyl derivatives. Keywords: cyclodextrins, monosubstitution, allyl, cinnamyl, formylmethyl, carboxymethyl
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