Synthesis of intermediate useful in the preparation of nojirimycin and related compounds
AssigneeMerrell Dow Pharmaceuticals Inc.
InventorPeter Anzeveno
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Abstract
5-Amino-5-deoxy-1,2-O-isopropylidene-.alpha.-D-glucofuranose is conveniently prepared by a hydride reduction of 5-azido-5-deoxy-1,2,O-isopropylidene-.alpha.-D-glucuronolactone and can readily be converted to nojirimycin, deoxynojirimycin or homonojirimycin.
Claims4
A process for preparing 5-amino-5-deoxy-1,2-O-isopropylidene-.alpha.-D-glucofuranose which comprises reducing 5-azido-azido-5-deoxy-1,2-O-isopropylidene-.alpha.-D-glucuronolactone with a hydride reducing agent selected from the group consisting of lithium aluminum hydride, lithium tri-t-butoxyaluminum hydride, and isobutylaluminum hydride.
A process for preparing nojirimycin which comprises reducing 5-azido-5-deoxy-1,2-O-isopropylidene-.alpha.-D-glucuronolactone with a hydride reducing, selected from the group consisting of lithium aluminum hydride, tri-t-butoxyaluminum hydride, and isobutylaluminum hydride, to give 5-amino-5-deoxy-1,2-O-isopropylidene-.alpha.-D-glucofuranose followed by reaction of the amino compound with aqueous sulfur dioxide to give nojirimycin bisulfite which is then converted to nojirimycin.
Dependencies are inferred from the claim text.