Deoxyuridine → 3',5'-o-Bis-tert-butyldimethylsilyl-2'-deoxyuridine

HRID 600113

Reaktionsgleichung

[C@@H:1]1([N:9]2[CH:16]=[CH:15][C:13](=[O:14])[NH:12][C:10]2=[O:11])[O:8][C@H:5]([CH2:6][OH:7])[C@@H:3]([OH:4])[CH2:2]1.[CH3:17][C:18]([Si:21](Cl)([CH3:23])[CH3:22])([CH3:20])[CH3:19]>CN(C=O)C>[Si:21]([C@@:3]1([OH:4])[C@@H:5]([CH2:6][O:7][Si:21]([C:18]([CH3:20])([CH3:19])[CH3:17])([CH3:23])[CH3:22])[O:8][C@@H:1]([N:9]2[CH:16]=[CH:15][C:13](=[O:14])[NH:12][C:10]2=[O:11])[CH2:2]1)([C:18]([CH3:20])([CH3:19])[CH3:17])([CH3:23])[CH3:22]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

Under a nitrogen atmosphere, a mixture of 2′-deoxyuridine dU (2.5 g, 10.95 mmol), TBSCl (7.26 g, 48.2 mmol) and imidiazole (6.56 g, 96.4 mmol) in anhydrous DMF (25 mL) was stirred at 0° C. for two hours and then warmed to room temperature over one hour. The reaction mixture was concentrated in vacuo and purified by silica gel column chromatography to yield 3′,5′-O-bis-tert-butyldimethylsilyl-2′-deoxyuridine dC.11 (4.62 g, 92%) as a white foam.

Aufarbeitung

temperaturewarmed to room temperature over one hour
concentrationThe reaction mixture was concentrated in vacuo
custompurified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag: ord-1737065a908c4e5d8435e94f91347f74
Quelldatensatz: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07897737B2

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