Process for producing 2,6-dideoxy-2-fluoro-L-talopyranose

Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives

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536 41, 536 64, C07H 100

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050345176

ABSTRACT:
2,6-Dideoxy-2-fluoro-L-talopyranose and 1-substituted derivatives thereof, including methyl 2,6-dideoxy-2-fluoro-L-talopyranoside and 3,4-di-O-protected-2,6-dideoxy-2-fluoro-L-talopyranosyl halides, are now provided and these new compounds are useful as intermediates for use in the synthesis of new compounds having antitumor activity, especially 7-O-(2,6-dideoxy-2-fluoro-.alpha.-L-talopyranosyl) daunomycinone or -adriamycinone. 2,6-Dideoxy-2-fluoro-L-talopyranose shows antibacterial activity. 2,6-Dideoxy-fluoro-L-talopyranose and the 1-substituted derivatives thereof may be produced by a multi-stage process starting from L-fucose.

REFERENCES:
Morrison et al., Organic Chemistry, 3rd ed. (1979), pp. 529, 564 and 636.

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