Scyllo-meso-Inosose

See Fletcher s review (Ref. 1, p. 62), where they are named epi-meso-inosose and scyllo-meso-inosose, respectively. 

In 1941 Posternak studied scyllo-meso-inosose (see p. 65), a penta-hydroxycyclohexanone which had been obtained by Kluyver and Bo-ezaardt from the biochemical oxidation of meso-inositol. Cautious oxidation of scyllo-meso-inoaose with permanganate led Posternak to the isolation of a hexaric acid which he identified as n,L-glucosaccharic acid. Since, of the two forms II and V, only II can give an optically inactive inosose oxidizable to D,L-glucosaccharic acid, this evidence appeared to settle the configuration of meso-inositol. 

Sprinson and Chargaff have reported that scyllo-meso-inosose in bicarbonate solution rapidly reduced six moles of periodic acid while in weakly acid solution the reaction was less complete. 

An interesting transition from the inositol to the quercitol series has recently been accomplished by Posternak. While hydrogenation of scyllo-meso-inosose with platinum oxide as a catalyst in neutral solution gave the expected mixture of meso-inositol and scyllitol, it was found that, when the reduction was carried out in dilute sulfuric acid solution, two moles of hydrogen rather than one were consumed and the product was a desoxyinositol, presumably the symmetrical form XLIX. That this reaction does not proceed through an inositol is shown by the stability of mcso-inositol under the conditions of the experiment. 

The configuration meso(135/24) was established by chemical correlation with scyllo-inosose. 

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