Abstract
Oxidation of 1,5-anhydro- d-mannitol with sodium metaperiodate, followed by nitromethane cyclization and benzylidenation afforded 1,5-anhydro-3-nitrohexitol derivatives having the d- gluco, d- manno, and d- galacto configurations. Conversion of the nitro alcohols into the nitro alkenes was accompanied by double-bond migration of the nitro 2,3-alkenes to give the 1,2-unsaturated derivatives.
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