2,5:3,4-Dianhydro-1,6-dideoxy-6-(trimethylamino)-d-allitol and -d-galactitol

A new, four-step synthesis of 2,5:3,6-dianhydro-1-deoxy-d-glucitol 16 was worked out, starting from 1,6-dibromo-1,6-dideoxy-d-mannitol. Compound 16 was converted into different 4-O-acyl derivatives, the 3,6-anhydro rings of which where opened with hydrogen bromide, yielding the corresponding 6-bromo compounds. These were converted, via the 6-azides, into the 6-(dimethylamino) derivatives, the sulfonic esters of which gave, on treatment with base, the 2,5:3,4-dianhydro-d-allitol and -d-galactitol derivatives. These were converted with methyl iodide into the corresponding quaternary salts. On biological testing, only the d-allitol derivative showed weak, muscarine-like activity.