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- Title
Oligonucleosides with a Nucleobase-Including Backbone. Part 12: Synthesis of Mixed Ethynylene-Linked Uridine- and Adenosine-Derived Tetramers.
- Authors
Simon Eppacher; Punit 4;Kumar Bhardwaj; Bruno Bernet; Jos 4;Luis Bravo 4;Gala; Thomas Knpfel; Andrea Vasella
- Abstract
In contradistinction to the corresponding Grignard reagent, bis[(trimethylsilyl)ethynyl]zinc reacted with the 5'-oxoadenosine 3 diastereoselectively to the -D-allo-hept-6-ynofuranosyladenine 5. Lithiation/iodination of the monomeric propargyl alcohol 5 and of the dimeric propargyl alcohol 22 provided the 8-iodoadenosines 7 and 18, respectively, considerably shortening the synthesis of the dimeric O-silylated 8-iodoadenosine 25. The mixed uridine- and adenosine-derived tetramers 21 and 32 were synthesised. The tetramer 21 was prepared by a linear sequence. Sonogashira coupling of 9 and 13 yielded the trimer 16 that was C-desilylated to 17. A second Sonogashira coupling of 17 and 19 yielded the tetramer 21. Tetramer 32 was prepared in higher yields by a convergent route, coupling the acetylene 29 and the iodide 30. The uridine-derived iodides proved more reactive than the adenosine-derived analogues, and the N6-unprotected adenosine-derived alkynes were more reactive than their N6-benzoylated analogues.
- Subjects
NUCLEOSIDES; ALCOHOL; ADENINE; ALCOHOLS (Chemical class); IODIDES
- Publication
Helvetica Chimica Acta, 2004, Vol 87, Issue 12, p2969
- ISSN
0018-019X
- Publication type
Article