Journal of Nucleic Acids / 2012 / Article / Sch 1

Review Article

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

Scheme 1

Synthesis of α,β-Dioxaphosphorinane-Constrained Nucleic Acid dinucleotides (α,β-D-CNA). Reagents and conditions: (i) TBDMSiCl, pyr, 95%; (ii) TBDPSiCl, imid, DMF, 97%; (iii) PTSA, MeOH, 95%; (iv) DCC, Cl2HCCOOH, DMSO then oxalic acid, 90%; (v) cat BiCl3, ZnI2, methyl acetate silylketene, DCM, 90%; (vi) NaBH4, EtOH, 85%; (vii) TsCl, CHCl3, pyr, 90; (viii) 5′-O-DMT-3′-O-diisopropylamino-cyanoethoxyphosphite thymidine, 1H-tetrazole, acetonitrile, then I2/H2O, 89%; (ix) Et3N, DMF, 90°C, 95%; (x) 3% TFA/DCM, 95%; (xi) TBAF, THF, 90%; (xii) (a) ω-t-butyldimethyl-silyloxy-allyltrimethylsilane, Et2O:BF3, DCM, (b) TiCl4, DCM, 60%; (xiii) (a) OsO4 cat, N-methylmorpholine N-oxide, H2O, (b) NaIO4, MeOH, (c) NaBH4, EtOH. 64%.

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