Monothioscyllitol-Ether als Discogen und Doppeldiscogen

Abstract

The ethers (3a, 4, and 5) of 1-deoxy-1-mercapto-scyllo-inositol (monothioscyllitol) and one ether (3b) of the hitherto unknown 1-deoxy-1-hydroseleno-scyllo-inositol (monoselenoscyllitol), a selenium analogue of the naturally occuring scyllo-inositol, have been prepared by nucleophilic substitution reaction from 2-O-mesyl-1,3,4,5,6-penta-O-benzyl-myo-inositol (2). Two of these derivatives S-hexyl-penta-O-benzyl-monothio-scyllitol (4) and the twin-compound S,S'-decamethylene-bis(penta-O-benzyl-monothio-scyllitol) (5) are the first scyllo-inositol ethers exhibiting mesophases (monotropic). Furthermore, the twin ether 5 is the first example of a novel type of geminal liquid crystals which contain two saturated alicyclic discogenic units bridged by a ten-carbon spacer between two sulfur atoms. This double-discogen 5 seems to form a novel type of mesophase.