Conformationally locked nucleoside analogs. Synthesis of 2'-Deoxy2′-C, 4′-C-bridged bicyclic nucleosides

Article abstract of DOI:10.1080/15257779908041488

1-a-Methylarabinose was converted, in three steps, to 2-deoxy-2-methyleneribose derivative 3, which was subjected to hydroboration to give 2-a-hydroxymethyl derivative 4 exclusively. 4 was converted to 2,4-bis(hydroxymethyl)ribose derivative 6 in four steps. Mesylation, detritylation, and ring closure, followed by hydrolysis of the mesyl group at OS, gave 3, 6-dioxabicyclo[3, 2, 1]octane derivative 8. After acetylation, 8 was coupled with silylated 6-chloropurine to give desired α- and β-bicyclic-sugar nucleosides. Copyright

Full text of DOI:10.1080/15257779908041488

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Conformationally Locked Nucleoside
Analogs. Synthesis of 2′-Deoxy-2′-C, 4′-
C-Bridged Bicyclic Nucleosides
Guangyi Wang a & Esmir Gunic a
a Research Department , ICN Pharmaceuticals, Inc. , 3300 Hyland
Avenue, Costa Mesa, California, 92626, U.S.A.
Published online: 04 Oct 2006.
To cite this article: Guangyi Wang & Esmir Gunic (1999) Conformationally Locked Nucleoside Analogs.
Synthesis of 2′-Deoxy-2′-C, 4′-C-Bridged Bicyclic Nucleosides, Nucleosides and Nucleotides, 18:4-5,
531-536, DOI: 10.1080/15257779908041488
To link to this article: http://dx.doi.org/10.1080/15257779908041488
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