Journal of Nucleic Acids / 2012 / Article / Sch 3

Review Article

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

Scheme 3

Synthesis of α,β,γ-Dioxaphosphorinane-Constrained Nucleic Acid dinucleotides (α,β,γ-D-CNA). Reagents and conditions: (i) HCOH, 2N NaOH, dioxane then NaBH4, 45%, (ii) DMTrCl, pyr, 70%, (iii) TsCl, CHCl3, Pyr, 90%, (iv) 3% TFA, DCM, quant. (v) 5′-O-DMT-3′-O-diisopropylamino-cyanoethoxyphosphite thymidine, 1H-tetrazole, acetonitrile, then I2/H2O, 80%, (vi) K2CO3, DMF, 90°C, 100%, (vii) TBAF, THF, 85%, and (viii) 3% TFA/DCM, quant.

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