Octitols, Nonitols, and Decitols

Four octitols, one nonitol, one decitol, and one dodecitol have been de-described. Of these only the configurations of the octitols are completely known. None occurs naturally. 

D-erythro-ij-gala-Octitol (XIX), m.p. 153°, [a]j, -f2.4° (H2O) octaacetate, m.p. 88-89°, Md +20.7° (CHCI3) has been synthesized by the reduction of the corresponding octoses obtained from D-glucose and from D-galactose by way of the cyanohydrin synthesis (84)- 

D-threo-L-gala-Octitol (XXII), m.p. 230 , [ ]d 0.0 (H2O), —0.5 (borax) octaacetate, m.p. 141 , [a] +40.4 (CHCI3) was obtained by reduction of the corresponding octose obtained from n-galactose by way of the cyanohydrin synthesis (86). 

A dodecitol has been isolated from the mother liquors of a mannitol preparation. Apparently it was formed by a reductive coupling of two molecules of glucose (86a). 

The deoxypolyols are not considered here the student is referred to the first edition of this text for an exposition of their synthesis and properties. 

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