Phosphorus oxide (P4O10) → 3'-O (2-tert-Butyldimethylsilylhydroxyethyl)adenosine

HRID 2229879Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2229879
[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

HCID 14812Phosphorus oxide (P4O10)HCID 24758Sodium hydrideHCID 60961AdenosineHCID 22592803(2-Bromoethyl)-t-butyldimethylsilane

Produkt 1

HCID 1317234073'-O (2-tert-Butyldimethylsilylhydroxyethyl)adenosine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

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

  1. stirringthe reaction mixture stirred at room temperature overnight
  2. customDMF was removed under vacuum and to the residue dichloromethane (100 mL)
  3. additionwas added
  4. washwashed with water (2×80 mL)
  5. dry with materialDichloromethane layer was dried over anhydrous Na2SO4
  6. customevaporated to dryness
  7. customResidue purified by column
  8. customto get

Quellen und Nachweise

ORD-Eintrag
ord-5d549d6778fa433f8362e47be44e7b20
Quelldatensatz
uspto-grants-2002_07
Patentnummer
US06420549B1

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