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Stereoselective synthesis of nucleosides by metallocene-promoted activation of glycosyl fluorides

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
33
Issue
8
Identifiers
DOI: 10.1016/s0040-4039(00)91869-0
Keywords
  • Metallocene Promoted Glycosylation
  • Nucleosides
  • Fluoronucleosides
  • Glycosyl Fluorides

Abstract

Abstract The Cp 2MCl 2-AgX (M=Hf, Zr; X=ClO 4, OTf) mixture is very effective for the promotion of the coupling of glycosyl fluorides and bis(trimethylsilyl)uracil. The stereoselectivity of the reaction depends on the solvent employed. Application to the synthesis of 1-(3,4 -isopropylidene-2-fluoro-2-O-methyl-α-D-ribopentopyranosyl)uracil is described.

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