Industrial Research Limited

John Adrian Dickison

Gary Brian Evans

Keith Clinch

Gavin Frank Painter

Ashley Jarvis

Paul Andrew Benjes

Anthony Mitchell

A novel method for the preparation of a compound of formula (I) from an N&#x2014;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&#x2014;protected-D-mannosamine, to give a 6&#x2014;O&#x2014;protected&#x2014;N&#x2014;protected-D-mannosamine; reducing the C-1 anomeric carbon atom of the 6&#x2014;O&#x2014;protected&#x2014;N&#x2014;protected-D-mannosamine to give a 6&#x2014;O&#x2014;protected&#x2014;N&#x2014;protected-D-mannitol; protecting the four hydroxyl groups of the 6&#x2014;O&#x2014;protected&#x2014;N&#x2014;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 Rand Rare 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 Ris hydrogen or a protecting group.

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Lower Hutt, New Zealand

John Adrian Dickison