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US 6,649,766 B2Granted
Process for the preparation of 1,5-dideoxy-1,5-imino hexitols from oximes or imines
AssigneeBoard of Trustees of Michigan State University
InventorsRawle I. Hollingsworth, Gabriela Pistia-Brueggeman
Life of this patent
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Abstract
A process for the preparation of 1,5-dideoxy-1,5-imino hexitols of a hexose sugars from novel hydroxyl protected oxime intermediates. The process includes formation of a lactam which is reduced to the hexitol. The hexitols are useful as drugs.
Claims4
A process for the preparation of a 1,5-imino, -1,5-dideoxy hexitol which comprises:
- (a) reacting a hydrazide of a 5-hexulosonic acid oxime or alkylimine with hydrogen and a hydrogenation catalyst in an acidic solvent at a temperature between about 20 and 80° C. and a pressure between about 200 and 400 psi to form a 5-imino-5-deoxyaldonic acid lactam;
- and
- (b) reducing the lactam with a reducing agent to form the 1,5-dideoxy-1,5-imino hexitol.
A process for the preparation of 1,5-imino-1,5-dideoxy D-glucitol as a product which comprises:
- (a) reacting L-xylo-5-hexulosonic acid hydrazide oxime with hydrogen and a palladium hydrogenation catalyst at a temperature between about 20 and 80° C. and a pressure between about 200 and 400 psi in glacial acetic acid to form a 5-imino-5-deoxyaldonic acid lactam;
- (b) reducing the lactain with a reducing agent to form the 1,5-imino-1,5-dideoxy D-glucitol.
Dependencies are inferred from the claim text.