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. Author manuscript; available in PMC: 2013 May 22.
Published in final edited form as: Nucleosides Nucleotides Nucleic Acids. 2009 Feb;28(2):67–77. doi: 10.1080/15257770902736426

SCHEME 3.

SCHEME 3

Synthesis of fully protected dG-C8-AP

Reaction conditions: a. Aqueous NBS, AcCN (78%); b. TBDMS-Cl, imidazole, DMF (90%); c. Bn-OH, PPh3, DIAD, dioxane (70%); d. DMT-Cl, pyridine (90%); e. Pd2(dba)3, BINAP, toluene, NaOtBu, 1-aminopyrene (48%); f. 0.02 M HCl in methanol (90%); g. Acetic acid, TBAF, THF (85%); h. Pd/C, cyclohexane, ethanol (90%); i. iBu anhydride, pyridine, TMCS (75%); j. DMT-Cl, DMAP, pyridine (84%); k. 2-Cyanoethyl-N,N-diisopropylchlorophosphoramidite, TEA, CH2Cl2, r.t., 1h (55%).