Process for the preparation of 1,5-(alkylimino)-1,5-dideoxy-D-gl

Details Process for the preparation of 1,5-(alkylimino)-1,5-dideoxy-D-gl Process for the preparation of 1,5-(alkylimino)-1,5-dideoxy-D-gl

1990-05-07

1992-09-29

Kilby Scalzo, Catherine S.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

546242, C07D21146

Patent

active

051515199

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.

REFERENCES:
patent: 4339585 (1982-07-01), Matsumura
patent: 4405714 (1983-09-01), Kinast et al.
patent: 4806650 (1989-02-01), Schroder et al.
patent: 4871747 (1989-10-01), Kinast et al.

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