ChemInform Abstract: Synthesis of New Chiral 18-Crown-6 Ethers from D-Xylose.
Abstract
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ChemInform Abstract
A facile and efficient synthesis of chiral 18-crown-6 ethers containing two furanoside moieties is presented. Compound (I), obtained from D-xylose, undergoes ether formation at the free hydroxyl group to give ethyleneoxyethyl bridged carbohydrate (III). Methanolysis of the isopropylidene protecting group of compound (III) affords a separable mixture of diastereomeric dihydroxides (V)-(VII), each suitable for ring closing reaction with diethylene glycol ditosylate (II). This method provides access to a wide variety of symmetrical or unsymmetrical chiral crown ethers containing two furanoside moieties.
