Z-Viburnitol

Sixteen pentahydroxycyclohexanes are predicted on the basis of stereochemical theory. The configuration of d-quercitol was limited to that shown below by nitric acid oxidation to galactaric (mucic) acid (8 ) and by alkaline permanganate oxidation to 3-deoxy-D-galactaric acid (metasaccharinic acid) (83), This same acid was obtained from Z-viburnitol (58), Hence, the arrangement of hydroxyl groups on carbon atoms 2, 5, and 6 of d-quercitol and Z-viburnitol must be the same. Another series of reactions also led to identical compounds from these two deoxyinositols (53), It was found that Acetobacter suboxydans catalyzed the oxidation of Z-viburnitol to a deoxy-... 

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