Synthesis p. 627 - 633 (1993)
Update date:2022-08-02
Topics:
Quaedflieg
Timmers
Van Der Marel
Kuyl-Yeheskiely
Van Boom
Reaction of deoxynucleoside 3'-O-(methylthiomethyl) acetals 1 with N-iodosuccinimide (NlS) 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(B(1Λ) B2) dimers 4. In addition, TMSOTf-promoted coupling of donor 6 (B1 = C(Bz)) 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 = C(Bz) and A(Bz)), to afford the corresponding trimers d(C(Λ)T(Λ)C) 11 and d(C(Λ)T(Λ)A) 12.
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Doi:10.1021/ja01541a072
(1958)Doi:10.1016/j.tetlet.2012.07.030
(2012)Doi:10.1016/j.dyepig.2013.09.046
(2014)Doi:10.1021/jacs.5b05575
(2015)Doi:10.1016/S0040-4039(00)74134-7
(1992)Doi:10.1016/j.bmcl.2012.06.086
(2012)