Carbohydrate Research p. 71 - 84 (1985)
Update date:2022-08-05
Topics:
Kuszmann, Janos
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.
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