C - Chemistry – Metallurgy – 07 – H
Patent
C - Chemistry, Metallurgy
07
H
C07H 19/00 (2006.01) C07H 11/00 (2006.01) C07H 19/073 (2006.01) C07H 19/173 (2006.01)
Patent
CA 2610283
A process of preparing an alpha-anomer enriched 2-deoxy-2,2- difluoro-D-ribofunanosyl sulfonate of formula (I) (see formula I) wherein each Y is independently selected from hydroxyl protecting groups, and R is an alkyl, substituted alkyl, aryl, or a substituted aryl group. The sulfonate of formula (I) 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.
L'invention concerne un procédé de préparation d'un 2-déoxy-2,2-difluoro-D-ribofuranosyl sulfonate enrichi en alpha-anomère, qui est utilisé comme produit intermédiaire dans la préparation d'un béta nucléoside, tel que la gemcitabine, qui est un agent antitumoral. Un béta-2-déoxy-2, 2-difluoro-D-ribofuranosyl sulfonate est chauffé et transformé en un alpha-2-déoxy-2, 2-difluoro-D- ribofuranosyl sulfonate, en l'absence d'une quantité efficace d'un sel sulfonate pour faciliter la conversion. En outre, un mélange anomère d'un alpha-anomère et d'un béta-anomère de 2-déoxy-2, 2-difluoro-D-ribofuranosyl sulfonate peut être dissous dans un mélange d'eau et d'un solvant et chauffé pour produire un lactol, qui peut ensuite être transformé en 2-déoxy- 2,2-difluoro-D-ribofuranosyl sulfonate enrichi en alpha-anomère.
Liu Allen
Schloemer George
Wang Lung-Hu
Moffat & Co.
Schloemer George
Scinopharm Taiwan Ltd.
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