Download PDF
Synthesis 1991; 1991(12): 1183-1190
DOI: 10.1055/s-1991-28417
paper
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

Synthesis of 2′,3′-Dideoxy-D-erythro-hexofuranosyl Nucleosides and 3′-Azido-2′, 3′-dideoxy-D-arabino-hexofuranosyl Nucleosides From Tri-O-acetyl-D-glucal via an α,β-Unsaturated Hexose Aldehyde

Jesper Lau* , Jesper Wengel, Erik B. Pedersen, Bent Faber Vestergaard
  • *Department of Chemistry, Odense University, DK-5230 Odense M, Denmark
Further Information

Publication History

Publication Date:
29 April 2002 (online)

  PDF Download  Permissions and Reprints All articles of this category

α,β-Unsaturated aldehyde 2 prepared from tri-O-acetyl-D-glucal was acetalated and benzoylated to give α,β-unsaturated acetal 6. Hydrogenation of the double bond followed by methanolysis resulted in methyl 2,3-dideoxyfuranosyl glycoside 8 which was used for nucleoside coupling with silylated N 6-isobutyrylcytosine and silylated thymine. Protected 3-azido-2,3-dideoxy-arabino-furanose 26 was prepared by 1,4-addition of hydrazoic acid to disilylated α,β-unsaturated aldehyde 24 followed by acetylation. Compound 26 was used for the preparation of 3′-azido-2′,3′-dideoxy-D-arabino-hexofuranosyl nucleosides 28 and 29.