2,5:3,4-DIANHYDRO-1,6-DIDEOXY-6-(TRIMETHYLAMINO)-D-ALLITOL AND -D-GALACTITOL

Article abstract of DOI:10.1016/S0008-6215(00)90734-1

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.