1,6-DIAMINO-2,5-ANHYDRO-1,6-DIDEOXY-DL-GLUCITOL AND SOME DERIVATIVES THEREOF

Article abstract of DOI:10.1016/S0008-6215(00)81795-4

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.