Carbohydrate Research p. 247 - 260 (1982)
Update date:2022-08-04
Topics:
Kuszmann, Janos
Pelczer, Istvan
1,6-Diamino-2,5-anhydro-1,6-dideoxy-DL-glucitol dihydrochloride and some derivatives were synthesized from 3,5-di-O-acetyl-1,6-dibromo-1,6-dideoxy-D-mannitol.Introduction of the 2,5-anhydro ring and subsequent replacement of the terminal bromine atoms by azide gave low yields of the diazide; therefore, a reverse reaction-sequence was applied.The azido groups were reduced with hydrogen sulfide-pyridine, and the amino groups formed were methylated by using formaldehyde-formic acid and subsequently treating with borohydride.According to 13C-n.m.r. investigations,the symmetrically substituted, 2,5-anhydroglucitol derivatives are present mainly in the 4T3 <"north" (N) type of twist> conformation, whereas the analogous L-iditol derivatives mainly adopt the 3T4 <"south" (S)> type.The different quaternary salts obtained on methylation of the corresponding 1,6-bis(dimethylamino)derivatives with methyl iodide (aiming at the structure of epi-muscarine) showed no muscarine-like, biological activity.
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