Abstract: A process for the preparation of 1,5-(alkylimino)-1,5-dideoxy-D-glucitol and derivatives of the formula: ##STR1## wherein R is hydrogen, alkyl of 1 to 13 carbon atoms, and aralkyl wherein alkyl is a lower alkyl of 2 to 6 carbon atoms, and aryl is phenyl, unsubstituted or substituted with lower alkyl of 1 to 6 carbon atoms, halo, lower alkoxy of 1 to 4 carbon atoms or thio lower alkyl of 1 to 4 carbon atoms by the steps of: treating L-sorbose with 2,2-dimethoxypropane to yield 1,2:4,6-di-O-(1-methylethylidene)-.alpha.-L-sorbanose; treating the compound with sulfuric acid in a solvent to produce 1,2-O-(1-methylethylidine)-.alpha.-L-sorbofuranose; consecutively treating with sulfonyl chloride and with an amine to yield 6-(substituted amino)-6-deoxy-1,2-O-(1-methylethylidine)-.alpha.-L-sorbofuranose; adsorbing the compound on an ion exchange resin and hydrogenating to produce compounds of the above formula.
Type:
Grant
Filed:
May 7, 1990
Date of Patent:
September 29, 1992
Assignee:
G. D. Searle & Co.
Inventors:
James R. Behling, Payman Farid, Ish Khanna, John R. Medich, Mike Prunier, Mike G. Scaros, Richard M. Weier