tert-Butyldimethylsilyl chloride → 9-[(2R,4R,5R)-4-[tert-butyl(dimethyl)silyl]-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-hydroxyoxolan-2-yl]-3H-purin-6-one

HRID 217571

반응식

HRID 217571 반응식
[CH3:1][C:2]([Si:5](Cl)([CH3:7])[CH3:6])([CH3:4])[CH3:3].[C@@H:9]1([N:17]2[C:26]3[N:25]=[CH:24][N:23]=[C:21]([OH:22])[C:20]=3[N:19]=[CH:18]2)[O:16][C@H:13]([CH2:14][OH:15])[C@@H:11]([OH:12])[CH2:10]1>CN(C=O)C>[Si:5]([C@@:11]1([OH:12])[C@@H:13]([CH2:14][O:15][Si:5]([C:2]([CH3:4])([CH3:3])[CH3:1])([CH3:7])[CH3:6])[O:16][C@@H:9]([N:17]2[C:26]3[N:25]=[CH:24][N:23]=[C:21]([OH:22])[C:20]=3[N:19]=[CH:18]2)[CH2:10]1)([C:2]([CH3:4])([CH3:3])[CH3:1])([CH3:7])[CH3:6]

참가 물질

4

반응물 2

HCID 28928tert-Butyldimethylsilyl chlorideHCID 178521064HCID 178521064, 화합물

생성물 1

HCID 1784552339-[(2R,4R,5R)-4-[tert-butyl(dimethyl)silyl]-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-hydroxyoxolan-2-yl]-3H-purin-6-one

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of TBSCl (1.91 g, 12.67 mmol) was added to a solution of 2′-deoxyinosine (1.00 g, 3.96 mmol) and imidiazole (1.73 g, 25.34 mmol) in anhydrous DMF (3 mL) at 0° C. under nitrogen atmosphere. The reaction mixture was gradually warmed to room temperature and stirred for 12 hours. The mixture was then concentrated in vacuo, dissolved in CH2Cl2 (100 mL), washed twice with water (50 mL), dried over anhydrous Na2SO4, concentrated in vacuo, and purified by silica gel chromatography to yield 3′,5′-O-bis-tert-butyldimethylsilyl-2′-deoxyinosine dA.n9 (1.58 g, 83%) as a white powder.

후처리

  1. concentrationThe mixture was then concentrated in vacuo
  2. dissolutiondissolved in CH2Cl2 (100 mL)
  3. washwashed twice with water (50 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated in vacuo
  6. custompurified by silica gel chromatography

출처 및 근거

ORD 기록
ord-84ad6101302d452794849dc43974e84d
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08198029B2

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