Methanol → 5'-O-(4,4'-Dimethoxytrityl)thymidine

HRID 3650

Reaktionsgleichung

Reaktionsgleichung von HRID 3650
C(N(CC)CC)C.[C@@H:8]1([N:16]2[CH:24]=[C:22]([CH3:23])[C:20](=[O:21])[NH:19][C:17]2=[O:18])[O:15][C@H:12]([CH2:13][OH:14])[C@@H:10]([OH:11])[CH2:9]1.[CH3:25][O:26][C:27]1[CH:48]=[CH:47][C:30]([C:31](Cl)([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[C:32]2[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=2)=[CH:29][CH:28]=1.CO>C1COCC1>[CH3:39][O:38][C:35]1[CH:34]=[CH:33][C:32]([C:31]([O:14][CH2:13][C@H:12]2[O:15][C@@H:8]([N:16]3[CH:24]=[C:22]([CH3:23])[C:20](=[O:21])[NH:19][C:17]3=[O:18])[CH2:9][C@@H:10]2[OH:11])([C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)[C:30]2[CH:47]=[CH:48][C:27]([O:26][CH3:25])=[CH:28][CH:29]=2)=[CH:37][CH:36]=1

Komponenten

6

Edukt 4

HCID 887MethanolHCID 5789ThymidineHCID 8471TriethylamineHCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)

Produkt 1

HCID 1624195'-O-(4,4'-Dimethoxytrityl)thymidineAusbeute 85,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Triethylamine (10 ml) in 200 ml THF was injected into a solid mixture of 6.8 g (28.0 mmol) thymidine and 10.2 g (28.6 mmol) 4,4'-dimethoxytrityl chloride under nitrogen with stirring. The solution was stirred at room temperature for 2 hours. After completion of the reaction, 10 ml methanol was added to consume the excess DMTrCl. The mixture was stirred for 5 minutes and the solvent removed by rotary evaporation. The residue was dissolved in 250 ml of ethyl acetate and the solution was washed with saturated NaHCO3 and dried over MgSO4. The solid was recrystallized from ethyl acetate/hexane to obtain 13.0 g 5'-protected thymidine 16 (85.6%).: m.p. 124°-126° C.; 1H NMR (200 MHz, CDCl3) δ8.97 (s, 1H, NH), 7.60 (m, 1H, H-6), 6.72-7.42 (m, 13H, Ph), 6.42 (m, 1H, H-1'), 4.56 (m, 1H, H-3'), 4.05 (m, 1H, H-4'), 3.78 (s, 6H, OMe2), 3.41 (m, 2H, H-5'), 2.62 (m, 1H, OH), 2.46 (m, 2H, H-2'), 1.46 (s, 3H, Me); 13C NMR (50 MHz, CDCl3) δ163.0 (C-4), 157.6, 149.8 (C-2), 143.5, 135.0 (C-6), 134.7, 134.6, 129.4, 127.4, 127.3, 126.5, 112.8, 110.9 (C-5), 86.7 (C-4'), 86.2, 84.7 (C-1'), 72.5 (C-3'), 63.8 (C-5'), 55.5 (OCH3), 41.3 (C-2'), 12.5 (CH3).

Aufarbeitung

  1. stirringThe solution was stirred at room temperature for 2 hours
  2. additionwas added
  3. customto consume the excess DMTrCl
  4. stirringThe mixture was stirred for 5 minutes
  5. customthe solvent removed by rotary evaporation
  6. dissolutionThe residue was dissolved in 250 ml of ethyl acetate
  7. washthe solution was washed with saturated NaHCO3
  8. dry with materialdried over MgSO4
  9. customThe solid was recrystallized from ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-2aa6ee52497c47eaaa4a3b64a6066424
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05734041

Verknüpfte Notizen

Wird geladen…