Process of making an alpha-anomer enriched...

Details Process of making an alpha-anomer enriched... Process of making an alpha-anomer enriched...

2006-05-24

2009-08-11

Lewis, Patrick T (Department: 1623)

Organic compounds -- part of the class 532-570 series

Organic compounds

Carbohydrates or derivatives

C536S018600

Reexamination Certificate

active

07572898

ABSTRACT:
A process of preparing an alpha-anomer enriched 2-deoxy-2,2-difluoro-D-ribofunanosyl sulfonate, which is useful as an intermediate in the preparation of a beta nucleoside, such as gemcitabine, an anti-tumor agent. A beta-2-deoxy-2,2-difluoro-D-ribofunanosyl sulfonate is heated and converted to an alpha-2-deoxy-2,2-difluoro-D-ribofunanosyl sulfonate in the absence of an effective amount of a sulfonate salt to facilitate the conversion. In addition, an anomeric mixture of an alpha-anomer and a beta-anomer of 2-deoxy-2,2-difluoro-D-ribofunanosyl sulfonate can be dissolved in a mixture of water and a solvent and heated to produce a lactol, which may be further converted to an alpha-anomer enriched 2-deoxy-2,2-difluoro-D-ribofunanosyl sulfonate.

REFERENCES:
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patent: 5606048 (1997-02-01), Chou et al.
Wallner et al. Tetrahedron (2005), vol. 61, pp. 1517-1521.

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