Chemical and Pharmaceutical Bulletin · 1963 · 11 citations · 0 references
Natural SciencesBiochemistryChemistryOrganic ChemistryOrganic SynthesisAcetaldehyde ChemistryAcetylenic AdditionGrignard Reagent SynthesisHydroxylationStereoselective HydroxylationStereoselective Sugar Synthesis
DL-Ribose was synthesized stereospecifically by oxidative hydroxylation of 2-ethoxy-5-(tetrahydro-2-pyranyloxy) methyl-2, 5-dihydrofuran (VII), which was obtained by hydrogenation of DL-1, 1-diethoxy-5-(tetrahydro-2-pyranyloxy)-2-pentyn-4-ol. DL-1, 1-diethoxy-5-(tetrahydro-2-pyranyloxy)-2-pentyn-4-ol was prepared by the Grignard reaction of (tetrahydro-2-pyranyloxy)acetaldehyde with propargyl diethyl acetal magnesium bromide.