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Practical synthesis of 2,6-dideoxy-D-lyxo-hexose ("2-deoxy-D-fucose") from D-galactose. 1998

C M Shafer, and T F Molinski
Department of Chemistry, University of California, Davis 95616, USA.

2,6-Dideoxy-D-lyxo-hexose was prepared efficiently from D-galactose in eight steps (25% overall yield). The synthesis is amenable to multigram scale-up.

UI MeSH Term Description Entries
D005643 Fucose A six-member ring deoxysugar with the chemical formula C6H12O5. It lacks a hydroxyl group on the carbon at position 6 of the molecule. Deoxygalactose,alpha-Fucose,alpha Fucose
D005690 Galactose An aldohexose that occurs naturally in the D-form in lactose, cerebrosides, gangliosides, and mucoproteins. Deficiency of galactosyl-1-phosphate uridyltransferase (GALACTOSE-1-PHOSPHATE URIDYL-TRANSFERASE DEFICIENCY DISEASE) causes an error in galactose metabolism called GALACTOSEMIA, resulting in elevations of galactose in the blood. D-Galactose,Galactopyranose,Galactopyranoside,D Galactose
D013237 Stereoisomerism The phenomenon whereby compounds whose molecules have the same number and kind of atoms and the same atomic arrangement, but differ in their spatial relationships. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) Molecular Stereochemistry,Stereoisomers,Stereochemistry, Molecular,Stereoisomer
D015394 Molecular Structure The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds. Structure, Molecular,Molecular Structures,Structures, Molecular

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