THE SYNTHESIS 0~ AMINO A~~AL&~uEs OF INOSITOL (INOSAMINES)"

In the course of work on the structure and configuration of streptamine (meso-l ,3-diamino-2,4,5,6-tetrahydroxycyclohexane) it seemed of interest to investigate the properties of the corresponding monoamino compounds (2,3 ,4,5,6-pentahydroxycyclohexylamines). We wish to propose the generic name inosamine for these amino analogues of inositol, since they are related to the inososes in the same way that glucamine is related to glucose. As one approach to the synthesis of inosamines, we have investigated the reduction of the phenylhydrazone (1, 2) and the oxime (2) of scylloinosose and the phenylhydrazone (3) of dl-epi-inosose. Each of these substances was hydrogenated readily at high pressures with Raney’s nickel as the catalyst, and the main product in each case consisted of an inosamine. The inosamines can exist theoretically in eight meso and twelve dl forms. However, the configuration of the five hydroxyl groups in each of the above inosose derivatives is fixed and known. Thus, unless unexpected C-O bond inversions occur during the hydrogenation, scyllo-inosose phenylhydrazone (I) or oxime (II) should give rise to not more than two inosamines (III, IV), each of which should have a meso configuration; and dl-epiinosose phenylhydrazone (V) should yield a maximum of two racemic forms (VI, VII). Experimentally, the inosamine from scyllo-inosose was obtained in two epimeric forms, each of which has been isolated in a pure state. Since the configuration of each epimer remains uncertain at the C-N bond, we have temporarily adopted the purely arbitrary names’ inosamine-SA and