5- O-Methyl-myo-inositol

Sequoyitol, which is optically inactive, was presumed to be one of the meso forms, and this presumption was eventually verified by the finding that the infrared spectrum of its pentaacetate differs from those of the (optically active) bornesitol pentaacetate and ononitol pentaacetate.66 Many unsuccessful attempts were made to decide between the two possibilities (LXXI and LXXII) by indirect means,78 83 by synthesis,164 and by degradation.68 Proof that sequoyitol is actually 5-O-methyl-myo-inositol (LXXI) was finally obtained by synthesizing it from (+)-pinitol.M The only myoinositol methyl ethers which could be derived from pinitol by the inversion of one of its hydroxyl groups are LXXI and LXXIV formula LXXIV is excluded because it must be optically active. The synthesis of sequoyitol from (+)-l, 2-anhydro-neoinositol (see p. 183) confirms the formula LXXI.7-166... 

Methyl ethers of several cyclitols occur as secondary substances in many higher plants. Attempts to use their occurrence for chemical taxonomy have been made (137). Sequoyitol (5-O-methyl-myo-inositol) is found in all families of gym-nosperms, and only in gymnosperms, although its distribution appears to be sporadic (137). It has been found in wood, bark, and cambial sap (114). D-Bornesitol (1-O-methyl-myo-inositol) is present in the latex of trees in the Apocynaceae family and in the wood of Sarcocephalus diderrichii (see 137). Dambonitol (1,3-di-O-methyl-myo-inositol) has been found in Gabon (Castilloa elastica) rubber latex (see 137). 

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