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

HRID 2229879Notes

Reaction equation

HRID 2229879 reaction equation
[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]

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

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)

Workup

  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

Sources & evidence

ORD record
ord-5d549d6778fa433f8362e47be44e7b20
Source dataset
uspto-grants-2002_07
Patent number
US06420549B1

Reaction notes

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