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Title:
PROCESSES FOR PREPARING 2-DIHALO RIBOLACTONES
Document Type and Number:
WIPO Patent Application WO/2017/075590
Kind Code:
A3
Abstract:
Methods for forming 2-bromo, 2-fluoro ribofuranose intermediates and 2-chloro, 2- fluoro ribofuranose intermediates for use in preparing antiviral nucleosides are disclosed. Methods for forming nucleosides, and nucleoside prodrugs, using the intermediates, are also disclosed. The methods all produce intermediates, and the resulting nucleosides and prodrugs thereof, wherein the chirality of the carbon at the 2-position is controlled. In some embodiments, the chemistry involves using chiral auxiliaries, such as (R)-2,2-dimethyl-l,3- dioxolane-4-carbaldehyde, and in other embodiments, the chemistry involves using chiral starting materials, such as D-xylose.

Inventors:
SARI OZKAN (US)
DE SCHUTTER CORALIE (US)
CHO JONG-HYUN (US)
ZHOU LONGHU (US)
ZANG HONGWANG (US)
AMBLARD FRANCK (US)
COATS STEVEN J (US)
SCHINAZI RAYMOND F (US)
Application Number:
PCT/US2016/059721
Publication Date:
July 20, 2017
Filing Date:
October 31, 2016
Export Citation:
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Assignee:
COCRYSTAL PHARMA INC (US)
UNIV EMORY (US)
International Classes:
C07D307/33; C07D413/12; C07D317/24; C07F7/18
Foreign References:
US20160024107A12016-01-28
Other References:
DAVIES STEPHEN G. ET AL.: "Double diastereoselective SuperQuat glycolate aldol reactions: Application to the asymmetric synthesis of polyfunctionalised lactones", ORG. BIOMOL. CHEM., vol. 2, no. 22, 2004, pages 3385 - 3400, XP055399684
MIKAMI KOICHI ET AL.: "Lanthanide(III) Catalyzed Aldol Reactions of Glyceraldehyde Acetonide with Ketene Silyl Acetals: Catalytic Asymmetric Route to Monosaccharides", TETRAHEDRON : ASYMMETRY, vol. 2, no. 10, 1991, pages 993 - 996, XP028086589
SHING TONY K. M. ET AL.: "Ruthenium-Catalyzed cis-Dihydroxylation of Alkenes: Scope and Limitations", CHEM. EUR. J., vol. 2, no. 1, 1996, pages 50 - 57, XP055388588
SHONO TATSUYA ET AL.: "Diastereoselective Addition of Electrogenerated Trichloromethyl and Dichloro(methoxycarbonyl)methyl Anions to a-Branching Aldehydes", J. AM. CHEM. SOC., 1984, pages 259 - 260, XP055399690
Attorney, Agent or Firm:
BRADIN, David (US)
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