Register      Login
Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

Cyclitols. XXX. The deamination of inosamines by nitrous acid

SJ Angyal and JS Murdoch

Australian Journal of Chemistry 22(11) 2417 - 2428
Published: 1969

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.

https://doi.org/10.1071/CH9692417

© CSIRO 1969

Committee on Publication Ethics


Export Citation Get Permission

View Dimensions