Journal of Nucleic Acids / 2012 / Article / Sch 4

Review Article

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

Scheme 4

Synthesis of δ, ε, ζ-Dioxaphosphorinane-Constrained Nucleic Acid dinucleotides (δ,ε,ζ-D-CNA). Reagents and conditions: (i) DMTrCl, DMAP, pyr, 90%, (ii) TBAF, THF, 95% and (iii) 5′-thymidine phosphoramidites, 1H-tetrazole, acetonitrile, then I2/H2O, 90%, (iv) 3% TFA, DCM, 95%, (v) Et3N, acetonitrile, 60°C, quant, and (vi) 1-(mesitylene-2-sulfonyl)-3-nitro-1,2,4-triazole (MSNT), pyr, 80°C, quant, (vii) TBAF, THF, 90%.
215876.sch.004

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