Abstract
Treatment of the sodium nitronate forms of 1-deoxy-1-nitrohexitols with methanolic sulfuric or hydrochloric acid at −30 °C leads to their regiospecific conversion to the corresponding methyl glycofuranosides. The reaction exhibits more pronounced stereoselectivity for 1-deoxy-1-nitroalditols with the 2,3- erythro configuration than with the 2,3- threo substrates and cis methyl glycofuranosides are the major products. The observed stereoselectivity indicates the lysis of the protonated aci-nitro form which is a two-step process consisting of nucleophilic addition to the protonated carbon–nitrogen double bond followed by the bimolecular nucleophilic substitution of the nitrogen-containing residue.
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