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Synthesis 1993; 1993(6): 627-633
DOI: 10.1055/s-1993-25915
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An Alternative Route to the Preparation of (3′ → 5′) Methylene Acetal Linked Di- and Trinucleosides

Peter J. L. M. Quaedflieg* , Cornelis M. Timmers, Gijs A. van der Marel, Esther Kuyl-Yeheskiely, Jacques H. van Boom
  • *Gorlaeus Laboratories, P.O. Box 9502, NL-2300 RA Leiden, the Netherlands
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Publikationsdatum:
17. September 2002 (online)

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Reaction of deoxynucleoside 3′-O-(methylthiomethyl) acetals 1 with N-iodosuccinimide (NIS) and dibutyl phosphate furnished the corresponding 3′-O-(dibutoxyphosphoryloxy)methyl acetals 6. Condensation of the latter with appropriately protected deoxynucleoside acceptors 3, in the presence of trimethylsilyl trifluoromethanesulfonate (TMSOTf), afforded in most cases the (3′ → 5′) methylene acetal linked d(B1 Υ B2) dimers 4. In addition, TMSOTf-promoted coupling of donor 6 (B1 = CBz) with 3′-O-(methylthiomethyl)thymidine (8) yielded dimer 9. Reaction of 9 with NIS and dibutyl phosphate gave dimer 10, which was applied successfully in the TMSOTf-assisted fusion with acceptors 3(B2 = CBz and ABz), to afford the corresponding trimers d(CΥTΥC) 11 and d(CΥTΥA) 12.

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