Synthesis of 2-deoxy-2-fluoro-D-mannose using fluoride ion.

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Abstract
Nucleophilic displacement reactions of the 3-O-acetyl, 3-O-methyl and 3-O-benzyl derivatives of methyl 4,6-O-benzylidene-2-O-(trifluoromethanesulfonyl)-.beta.-D-glucopyranoside with tetraalkylammonium fluorides in acetonitrile proceeded smoothly to give, with invesion of configuration at C2, the corresponding methyl 2-deoxy-2-fluoro-.beta.-D-mannopyranosides in good yields. Similar treatment of methyl 3-O-benzyl-4,6-O-benzylidene-2-O-(trifluoromethanesulfonyl)-.alpha.-D-glucopyranoside or methyl 3,4,6-tri-O-acetyl-2-O-(trifluoromethanesulfonyl)-.beta.-D-glucopyranoside resulted in decreased yield of the fluoro-manno compound. Efficient conversion of these fluorinated intermediates into 2-deoxy-2-fluoro-D-mannose (1) [a radiopharmaceutical for cancer diagnosis] in humans was achieved by heating with acidic reagents. These synthetic sequences could be easily adapted for the preparation of the 18F-labeled analog of (1).

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