Phosphorus oxide (P4O10) → 3'-O (2-tert-Butyldimethylsilylhydroxyethyl)adenosine
Reaktionsgleichung
[C@@H:1]1([N:10]2[C:19]3[N:18]=[CH:17][N:16]=[C:14]([NH2:15])[C:13]=3[N:12]=[CH:11]2)[O:9][C@H:6]([CH2:7][OH:8])[C@@H:4]([OH:5])[C@H:2]1[OH:3].[O:20]=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[H-].[Na+].Br[CH2:37][CH2:38][Si:39]([C:42]([CH3:45])([CH3:44])[CH3:43])([CH3:41])[CH3:40]>CN(C=O)C.C(Cl)Cl.CO>[Si:39]([CH:38]([OH:20])[CH2:37][O:5][C@@H:4]1[C@@H:6]([CH2:7][OH:8])[O:9][C@@H:1]([N:10]2[C:19]3[N:18]=[CH:17][N:16]=[C:14]([NH2:15])[C:13]=3[N:12]=[CH:11]2)[C@@H:2]1[OH:3])([C:42]([CH3:45])([CH3:44])[CH3:43])([CH3:41])[CH3:40]Komponenten
8
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 3
Versuchsvorschrift
Adenosine (10 g, 37.42 mmol) was dried over P2O5 under high vacuum. It was then suspended in anhydrous DMF (150 mL) and NaH (1.35 g, 56.13 mmol) was added. The reaction mixture was stirred at room temperature under inert atmosphere for 30 min. Then (2-bromo ethyl)-tert-butyldimethylsilane (9.68 mL, 4.4.90 mmol) was added dropwise and the reaction mixture stirred at room temperature overnight. DMF was removed under vacuum and to the residue dichloromethane (100 mL) was added and washed with water (2×80 mL). Dichloromethane layer was dried over anhydrous Na2SO4 and evaporated to dryness. Residue purified by column to get a mixture of the title compounds (4.30 g). Rf 0.49, 0.57 (10% MeOH in CH2Cl2)
Aufarbeitung
- stirringthe reaction mixture stirred at room temperature overnight
- customDMF was removed under vacuum and to the residue dichloromethane (100 mL)
- additionwas added
- washwashed with water (2×80 mL)
- dry with materialDichloromethane layer was dried over anhydrous Na2SO4
- customevaporated to dryness
- customResidue purified by column
- customto get
Quellen und Nachweise
- ORD-Eintrag
- ord-ecad48429eb141fb9aece343ce6fa8fb
- Quelldatensatz
- uspto-grants-2005_02
- Patentnummer
- US06849723B2
Notizen zur Reaktion
Wird geladen…