Cyclitols. XXX. The deamination of inosamines by nitrous acid

Abstract

The deamination of inosamines with nitrous acid gives a mixture from which only small amounts of inositols can be isolated. However, L-1- amino-1-deoxy-chiro-inositol yields the epoxide, L-1,2-anhydro-myo- inositol, in 60% yield. The penta-O-acetates of the inosamines give inositols in good yield; in several cases the penta-O-acetyl inositols were isolated. The extent of inversion in this displacement reaction varies with the configuration of the inosamine from complete inversion to predominant retention of configuration. Elimination also occurs during deamination and results in the formation of an enol acetate. Hydrogenation of 3-deoxy-3-nitro-muco-inositol in neutral solution gives mainly 3-amino-3-deoxy-epi-inositol.