Carbohydrate Research 2011-11-08

Complete sets of monosubstituted cyclomaltohexaoses (α-cyclodextrins) as precursors for further synthesis.

Michal Rezanka, Jindřich Jindřich

Index: Carbohydr. Res. 346(15) , 2374-9, (2011)

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Abstract

Alkylation of cyclomaltohexaose (α-cyclodextrin, α-CD) with allyl or cinnamyl bromide, followed by peracetylation of remaining hydroxyl groups and separation of isomers, resulted in the set of peracetylated 2(I)-O-, 3(I)-O- and 6(I)-O-alkylated α-CDs in up to 27% yields. Ozonolysis or oxidative cleavage of peracetylated allyl or cinnamyl derivatives resulted in a complete set of peracetylated 2(I)-O-, 3(I)-O- and 6(I)-O-formylmethyl or carboxymethyl derivatives that are useful precursors for preparation of regioselectively monosubstituted derivatives of α-CD. Moreover, a quick method to recognize single 2(I)-O-, 3(I)-O- and 6(I)-O-monosubstituted peracetylated CDs from one another using only their (1)H NMR spectra has been proposed.Copyright © 2011 Elsevier Ltd. All rights reserved.