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

HRID 2229879노트

반응식

HRID 2229879 반응식
[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]

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 887Methanol용매HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

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)

후처리

  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

출처 및 근거

ORD 기록
ord-5d549d6778fa433f8362e47be44e7b20
출처 데이터셋
uspto-grants-2002_07
특허 번호
US06420549B1

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