D‐Galacturonsäurederivate, VI. D‐Galacturonsäurederivate mit flüssigkristallinen Eigenschaften

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Abstract
D‐Galacturonic Acid Derivatives, VI. — D‐Galacturonic Acid Derivatives with Liquid Crystalline PropertiesEsters, thioesters, and amides of D‐galacturonic acid have been synthesized from alcohols, thioalcohols, and amines having long alkyl chains. Key intermediate of the reaction with the different nucleophiles was the 1,2;3,4‐di‐O‐isopropylidene‐α‐D‐galactopyranuronosyl chloride (3). Deisopropylidenation of the protected esters, thioesters, and amides was achieved by trifluoroacetic acid. The investigation of the liquid crystalline properties was carried out with a polarizing microscop, DSC measurements, and X‐ray diffraction. Molecules with three long alkyl chains can be obtained by reaction of amides 5h and 5i with thioalcohols. MM2 calculations voted a Y‐shaped structure of the mercaptals 8a and 8b which do exhibit thermotropically a columnar hexagonal mesophase (Dhd) as we have proved by X‐ray diffraction.

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