Download PDF
Synthesis 1993; 1993(6): 627-633
DOI: 10.1055/s-1993-25915
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.

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
Further Information

Publication History

Publication Date:
17 September 2002 (online)

  PDF Download  Permissions and Reprints All articles of this category

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.