Abstract
DL-(1, 3/2)-3-Acetamido-1, 2-di-O-benzylcyclohex-4-enediol (IIIa) and DL-(1, 3/4)-1-ace-tamido-3, 4-di-O-benzylcyelohex-5-enediol (IIIb) were synthesized from DL-trans-1, 2-di-O-benzylcyclohex-3-enediol (I) via the corresponding azide derivatives (IIa-b) prepared by bromination and subsequent treatment with sodium azide in N, N-dimethylformamide. Compounds (IIIa and IIIb) were converted into a variety of deoxyinosamine and deoxyinosadiamine derivatives via epoxides (VIII and IX) or by cis-hydroxylation with osmium tetroxide. Hexaacetyl-rac-inosamine-1 (XVIIIc) was synthesized from DL-(1, 3, 4/2, 5)-3-acetamido-1, 2-di-O-benzyl-5-bromocyclohexanetriol (VIa) via conduramine derivatives (XVIIa-c). Conformational analysis of partially O-benzylated aminocyclitol derivatives were studied by means of NMR spectroscopy.
