J. Kuszmann, I. Pelczer
Feb 16, 1981
Citations
0
Influential Citations
9
Citations
Journal
Carbohydrate Research
Abstract
Abstract 1,6-Diamino-2,5-anhydro-1,6-dideoxy- l -iditol ( 31 ) and its derivatives were synthesized, starting from 2,4- O -benzylidene-1,6-di- O -tosyl- d -glucitol. The 1,6-bis-(acetamido)- l - talo epoxide was readily hydrolyzed to the corresponding l -iditol derivative under anchimeric assistance of the 1-acetamido group. On treatment with formaldehyde-formic acid, diamine 31 gave a tricyclic, 1,4:3,6-bis( N , O -methylene) derivative which was stable under acidic conditions but, according to 13 C-n.m.r. spectroscopy, was readily hydrolyzed to an equilibrium mixture in neutral, aqueous solution. The corresponding 1,6-bis(dimethylamino) derivative could be obtained by reducing this equilibrium mixture with borohydride. The different, quaternary salts obtained on methylation of the corresponding 1,6-bis(dimethylamino) derivatives with methyl iodide (aiming at the structure of epi - allo -muscarine) showed no muscarine-like, biological activity.