Preparation of the C-ribose-labeled 2′--TOM protected ribonucleoside phosphoramidites –

<p><b>Copyright information:</b></p><p>Taken from "Short, synthetic and selectively C-labeled RNA sequences for the NMR structure determination of protein–RNA complexes"</p><p>Nucleic Acids Research 2006;34(11):e79-e79.</p><p>Published online 28 Jun 2006</p><p>PMCID:PMC1904103.</p><p>© 2006 The Author(s)</p> Abbreviations: Ac = acetyl, Bz = benzoyl, Ibu = isobutyryl, CE = cyanoethyl, DMT = (4,4′-dimethoxy)trityl, TOM = (triisopropylsilyl)oxymethyl. Reagents and conditions: () Adapted from Saito (), detailed procedure in Supplementary Data: 1. FeCl, MgSO, acetone, 20°; 2. pyridinium dichromate, AcO, CHCl, reflux; 3. HIO, THF, 20°; 4. NaBH, THF/EtOH 1:1, 20°; 5. BzCl, pyridine, 20°; 6. AcO, AcOH, HSO, 20°. () 6-Chloro--isobutyrylpurine-2-amine, ,-bis(trimethylsilyl)acetamide (BSA), MeSiOTf, 1,2-dichloroethane, 65°. () 1. Allyl alcohol, DABCO, DBU, 20°; 2. NaOH, THF/MeOH/HO, 0°; 3. DMT-Cl, pyridine, 20°. () Pd(PhP), HNEt, PPh, CHCl, 20°. () Synthesis of : 1. -benzoyladenine, BSA, SnCl, 1,2-dichloroethane, 65°; 2. NaOH, THF/MeOH/HO, 0°; 3. DMT-Cl, pyridine, 20°; synthesis of : 1. uracil, BSA, MeSiOTf, MeCN, 60°; 2. MeNH, EtOH, 20°; 3. DMT-Cl, pyridine, 20°. () BuSnCl, PrNEt, TOM-Cl, 1,2-dichloroethane, 80° according to (). () 1. AcO, DMAP, pyridine 25°; 2. 4-chlorophenyl phosphorodichloridate, 1-1,2,4-triazole, PrNEt, MeCN, 4° → 20°; 3. aqueous NH, dioxane/MeCN, 20°; 4. NaOH, THF/MeOH/HO, 4° 5. AcO, DMF, 20°, according to (). () 2-Cyanoethyldiisopropylphosphoramidochloridite, PrNEt, CHCl, 20°, according to ()