Process for preparing kifunensine intermediate and...

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

Reexamination Certificate

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C549S377000, C549S448000

Reexamination Certificate

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07129355

ABSTRACT:
A novel method for the preparation of a compound of formula (I) from an N—protected-D-mannosamine. A compound of formula (I) is a useful intermediate for the preparation of kiftnensine, a potent and selective mannosidase inhibitor. The method includes protecting the hydroxyl group at the C-6 position of an N—protected-D-mannosamine, to give a 6—O—protected—N—protected-D-mannosamine; reducing the C-1 anomeric carbon atom of the 6—O—protected—N—protected-D-mannosamine to give a 6—O—protected—N—protected-D-mannitol; protecting the four hydroxyl groups of the 6—O—protected—N—protected-D-mannitol; and removing the nitrogen atom protecting group and optionally removing the C-6 oxygen atom protecting group to give the compound of formula (I):where R1and R2are each independently protecting groups which, together with the oxygen atoms to which they are attached, form a 5-, 6-, 7- or 8-membered ring; and R3is hydrogen or a protecting group.

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