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Thymidine → 5'-O-(4,4'-di-3,5-hexadienoxytrityl)thymidine

HRID 363546
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 363546
[CH2:1]([O:7][C:8]1[CH:34]=[CH:33][C:11]([C:12]([OH:32])([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][CH:22]=[CH:23][CH:24]=[CH2:25])=[CH:15][CH:14]=2)=[CH:10][CH:9]=1)[CH2:2][CH:3]=[CH:4][CH:5]=[CH2:6].C(Cl)(=O)C.[C@@H:39]1([N:47]2[CH:55]=[C:53]([CH3:54])[C:51](=[O:52])[NH:50][C:48]2=[O:49])[O:46][C@H:43]([CH2:44]O)[C@@H:41]([OH:42])[CH2:40]1.CN(C1N=CC=CN=1)C>C1(C)C=CC=CC=1.N1C=CC=CC=1>[CH2:1]([O:7][C:8]1[CH:34]=[CH:33][C:11]([C:12]([O:32][CH2:44][C@H:43]2[O:46][C@@H:39]([N:47]3[CH:55]=[C:53]([CH3:54])[C:51](=[O:52])[NH:50][C:48]3=[O:49])[CH2:40][C@@H:41]2[OH:42])([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][CH:22]=[CH:23][CH:24]=[CH2:25])=[CH:15][CH:14]=2)=[CH:10][CH:9]=1)[CH2:2][CH:3]=[CH:4][CH:5]=[CH2:6]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 5789ThymidineHCID 6367Acetyl chlorideHCID 5217172-DimethylaminopyrimidineHCID 538662944,4'-Di-3,5-hexadienoxytrityl alcohol

Produkt 1

HCID 538107565'-O-(4,4'-di-3,5-hexadienoxytrityl)thymidineAusbeute 84,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049
Pyridine
Lösungsmittel
2×
HCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

Compound 30 (3.5 grams, 7.73 mmol) was coevaporated with toluene (2×) and then dissolved in anhydrous toluene (85 mL). Acetyl chloride (33 mL, 464 mmol) was added to the solution and the reaction mixture was heated to reflux and stirred under argon. After 4 hours the reaction mixture was concentrated in vacuo and the crude product was coevaporated with pyridine and then dissolved in anhydrous pyridine (42 mL). Thymidine (1.5 grams, 6.18 mmol), which had been coevaporated with pyridine and dissolved in anhydrous pyridine (42 mL), was then added to the solution containing the crude product. A catalytic amount of dimethylaminopyrimidine (DMAP) was added and the reaction mixture was stirred under argon overnight and the solvent was evaporated. The residue was redissolved in dichloromethane and washed with a 5% aqueous solution of sodium bicarbonate followed by water. The organic phase was dried (MgSO4), evaporated and purified by column chromatography (silica gel; EtOAc/hexane, 1/1) to afford 3.53 grams (84%) of compound 31 as an off-white solid. 1H NMR (300 MHz, CDCl3) δ1.47 (s, 3H), 2.22-2.46 (m, 2H), 2.50-2.63 (m, 4H), 3.35-3.58 (m, 2H), 3.85-4.09 (m, 5H), 4.51-4.60 (m, 1H), 5.02 (dd, J=1.5, 10.4 Hz, 2H), 5.14 (dd, J=1.5, 17.3 Hz, 2H), 5.68-5.83 (m, 2H), 6.12-6.45 (m, 5H), 6.82 (d, J=9.0 Hz, 4H), 7.18-7.46 (m, 9H), 7.58 (s, 1H), 8.44 (s, 1H); Anal. Calcd for C41H44N2O7.2H2O (712.8384): C, 69.08; H, 6.79; H, 3.93. Found: C, 69.34; H, 6.44; N, 3.91.

Aufarbeitung

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux
  3. concentrationAfter 4 hours the reaction mixture was concentrated in vacuo
  4. dissolutiondissolved in anhydrous pyridine (42 mL)
  5. additionwas then added to the solution
  6. stirringthe reaction mixture was stirred under argon overnight
  7. customthe solvent was evaporated
  8. dissolutionThe residue was redissolved in dichloromethane
  9. washwashed with a 5% aqueous solution of sodium bicarbonate
  10. dry with materialThe organic phase was dried (MgSO4)
  11. customevaporated
  12. custompurified by column chromatography (silica gel; EtOAc/hexane, 1/1)

Quellen und Nachweise

ORD-Eintrag
ord-acfb2908d8b6438990badfd1e4ba90e9
Quelldatensatz
uspto-grants-1999_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05874532

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