Journal of Nucleic Acids / 2012 / Article / Sch 2

Review Article

Dioxaphosphorinane-Constrained Nucleic Acid Dinucleotides as Tools for Structural Tuning of Nucleic Acids

Scheme 2

Synthesis of α,β-Phostone-Constrained Nucleic Acid dinucleotides (α,β-P-CNA). Reagents and conditions: (i) allyltrimethylsilane, BF3 : Et2O, 90%, (ii) Me3SiCl, pyr, rt, 3 h, 95%, (iii) BH3 : Me2S, THF, rt, 2 h then NaOH/H2O2, rt, 0.5 h, 90%, (iv) TsCl, CHCl3, pyr, rt, 16 h, 85%, (v) PTSA, MeOH, rt, 1 h, 90%, (vi) thymidine phosphoramidite,1H-tetrazole, rt, 81%, (vii) LiBr, acetonitrile, 90°C, MW 3 h, 85%, and (viii) 3%TFA, CH2Cl2, then TBAF, THF, rt, 1 h, 90%.

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