Functionalizing carbohydrate derivatives by base-induced .beta.-eliminatiom forming bioactive derivatives containing hydroxy-diene subunits

A process for functionalizing a 2-deoxyfuranose derivative comprising:

• coupling a first substituted and protected 2-deoxyfuranose derivative with a first coupling reagent to yield a second substituted and protected 2-deoxyfuranose derivative;
• deprotecting said second substituted and protected 2-deoxyfuranose derivative to yield a substituted and deprotected 2-deoxyfuranose derivative, said substituted and deprotected 2-deoxyfuranose being characterized as having a free hydroxyl group at its C-1 position;
• and
• coupling said substituted and deprotected 2-deoxyfuranose derivative with a second coupling reagent, thereby effecting a base-induced .beta.-elimination and subsequent olefination to form a derivative of .alpha.-hydroxy-diene fatty acid.

A process for functionalizing a 2-deoxypyranose derivative comprising:

• coupling a first substituted and protected 2-deoxypyranose derivative with a first coupling reagent to yield a second substituted and protected 2-deoxypyranose derivative;
• deprotecting said second substituted and protected 2-deoxypyranose derivative to yield a substituted and deprotected 2-deoxypyranose derivative, said substituted and deprotected 2-deoxypyranose being characterized as having a free hydroxyl group at its C-1 position;
• and
• coupling said substituted and deprotected 2-deoxypyranose derivative with a second coupling reagent, thereby effecting a base-induced .beta.-elimination and subsequent olefination to form a derivative of an .alpha.,.beta.-dihydroxy-diene fatty acid.

A process for the preparation of a derivative of fatty acid containing a subunit having at least one hydroxyl group and a diene group comprising:

• coupling a first substituted and protected carbohydrate derivative with a first coupling reagent to yield a second substituted and protected carbohydrate derivative;
• deprotecting said second substituted and protected carbohydrate derivative to yield a substituted and deprotected carbohydrate derivative, said substituted and deprotected carbohydrate derivative being characterized as having a free hydroxyl group at its C-1 position;
• and
• coupling said substituted and deprotected carbohydrate derivative with a second coupling reagent, thereby effecting a base-induced .beta.-elimination and subsequent olefination.

A process for the preparation of a derivative of fatty acid containing an .alpha.-hydroxy-diene subunit comprising:

• coupling a first substituted and protected 2-deoxy-furanose derivative with a first coupling reagent to yield a second substituted and protected 2-deoxyfuranose derivative;
• deprotecting said second substituted and protected 2-deoxyfuranose derivative to yield a substituted and deprotected 2-deoxyfuranose derivative, said substituted and deprotected 2-deoxyfuranose derivative being characterized as having a free hydroxyl group at its C-1 position;
• and
• coupling said substituted and deprotected 2-deoxyfuranose derivative with a second coupling reagent, thereby effecting a base-induced .beta.-elimination and subsequent olefination.

A process for the preparation of a derivative of fatty acid containing an .alpha., .beta.-dihydroxy-diene subunit comprising:

• coupling a first substituted and protected 2-deoxypyranose derivative with a first coupling reagent to yield a second substituted and protected 2-deoxypyranose derivative;
• deprotecting said second substituted and protected 2-deoxypyranose derivative to yield a substituted and deprotected 2-deoxypyranose derivative, said substituted and deprotected 2-deoxypyranose derivative being characterized as having a free hydroxyl group at its C-1 position;
• and
• coupling said substituted and deprotected 2-deoxypyranose derivative with a second coupling reagent, thereby effecting a base-induced .beta.-elimination and subsequent olefination.

A process for the preparation of a derivative of fatty acid containing a subunit having at least one hydroxyl group and a diene group comprising:

• coupling a substituted carbohydrate derivative, having a first free hydroxyl group at its C-1 position, with a first coupling reagent to yield a substituted diene derivative having a second free hydroxyl group generated from ring opening of said substituted carbohydrate derivative;
• protecting said second free hydroxyl group in said substituted diene derivative to yield a substituted and protected diene derivative;
• coupling said substituted and protected diene derivative with a second coupling reagent, thereby effecting a base-induced .beta.-elimination and subsequent olefination to form a protected precursor;
• and
• deprotecting said protected precursor.

A process for functionalizing a carbohydrate derivative comprising:

• coupling a substituted carbohydrate derivative, having a first free hydroxyl group at its C-1 position, with a first coupling reagent to yield a substituted diene derivative having a second free hydroxyl group generated from ring opening of said substituted carbohydrate derivative;
• protecting said second free hydroxyl group in said substituted diene derivative to yield a substituted and protected diene derivative;
• coupling said substituted and protected diene derivative with a second coupling reagent, thereby effecting a base-induced .beta.-elimination and subsequent olefination to form a protected precursor;
• and
• deprotecting said protected precursor to give a compound containing a subunit having at least one free hydroxyl group and a diene group.