Process for preparing 2',2'-difluoronucleosides

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

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536 272, 536 276, 536 2761, 536 2762, 536 2763, 536 2781, 536 281, 536 283, 536 284, 536 285, 536 2852, 536 2853, 536 2854, 536 2855, C07H 1900

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054342546

ABSTRACT:
The present invention provides a process for preparing lactone intermediates to 2',2'-difluoronucleosides whereby reversion back to the lactone's open chain precursor is minimized and the desired erythro enantiomer can be selectively isolated from an enantiomeric mixture of erythro and threo lactones in crystalline form. Also provided is a process for producing 2'-deoxy-2',2'-difluoronucleosides in about a 1:1 .alpha./.beta. anomeric ratio, and processes for selectively isolating .beta.-2'-deoxy-2',2'-difluorocytidine, or an organic or inorganic acid addition salt thereof, from the 1:1 .alpha./.beta. mixture.

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Encyclopedia of Polymer Science and Engineering, Second Ed., H. F. Mark et al., eds., John Wiley and Sons, New York, vol. 8, p. 346 (1987).

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