Synthesis of 3-deoxy-3-C-trifluoromethyl-D-ribose from D-xylose or D-glucose

Article abstract of DOI:10.1080/07328309608005659

The synthesis of 3-deoxy-1,2-O-isopropylidene-3-C-trifluoromethyl-α-D-ribofuranose is described. After a first approach from a commercial D-xylose derivative which was limited by an incomplete stereoselectivity, the synthesis of the title compound was performed from 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose by a reaction sequence where key steps: trifluoromethylation with CF₃SiMe₃ and radical deoxygenation are highly stereoselective.

Full text of DOI:10.1080/07328309608005659

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Synthesis of 3-Deoxy-3-C-
Trifluoromethyl-d-Ribose From d-Xylose
or d-Glucose
S. Lavaire a , R. Plantier-Royon a & C. Portella a
a Laboratoire des Réarrangements Thermiques et Photochimiques,
Associé au CNRS , UFR Sciences Exactes et Naturelles , BP 1039,
51687, Reims Cedex, 2, France
Published online: 22 Aug 2006.
To cite this article: S. Lavaire , R. Plantier-Royon & C. Portella (1996) Synthesis of 3-Deoxy-3-C-
Trifluoromethyl-d-Ribose From d-Xylose or d-Glucose, Journal of Carbohydrate Chemistry, 15:3,
361-370, DOI: 10.1080/07328309608005659
To link to this article: http://dx.doi.org/10.1080/07328309608005659
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