Dimethylformamide → 3',5'-o-Bis-tert-butyldimethylsilyl-2'-deoxycytidine

HRID 600111

反応式

HRID 600111 の反応式
[C@@H:1]1([N:9]2[CH:16]=[CH:15][C:13]([NH2:14])=[N:12][C:10]2=[O:11])[O:8][C@H:5]([CH2:6][OH:7])[C@@H:3]([OH:4])[CH2:2]1.[CH3:17][C:18]([Si:21](Cl)([CH3:23])[CH3:22])([CH3:20])[CH3:19].CN(C=O)C>CO>[Si:21]([C@@:3]1([OH:4])[C@@H:5]([CH2:6][O:7][Si:21]([C:18]([CH3:20])([CH3:19])[CH3:17])([CH3:23])[CH3:22])[O:8][C@@H:1]([N:9]2[CH:16]=[CH:15][C:13]([NH2:14])=[N:12][C:10]2=[O:11])[CH2:2]1)([C:18]([CH3:20])([CH3:19])[CH3:17])([CH3:23])[CH3:22]

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 13711DeoxycytidineHCID 28928tert-Butyldimethylsilyl chloride

生成物 1

HCID 1317287263',5'-o-Bis-tert-butyldimethylsilyl-2'-deoxycytidine

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

2′-deoxycytidine dC (2.85 g, 12.54 mmol), imidiazole (6.49 g, 95.31 mmol), and TBSCl (7.18 g, 47.65 mmol) were added to anhydrous DMF (27 mL) and stirred at room temperature overnight under a N2 atmosphere. Methanol (20 mL) was added, and the mixture was stirred for 30 minutes and then concentrated in vacuo. Ethyl acetate (60 mL) and water (60 mL) were then added. The organic layer was separated and washed twice with water (20 mL), and the combined aqueous layer was extracted with ethyl acetate (20 mL). The combined organic layer was dried with Na2SO4, concentrated in vacuo, and purified by silica gel chromatography to give 3′,5′-O-bis-tert-butyldimethylsilyl-2′-deoxycytidine dC.01 (4.79 g, 84%) as a white foam.

後処理

  1. stirringthe mixture was stirred for 30 minutes
  2. concentrationconcentrated in vacuo
  3. additionEthyl acetate (60 mL) and water (60 mL) were then added
  4. customThe organic layer was separated
  5. washwashed twice with water (20 mL)
  6. extractionthe combined aqueous layer was extracted with ethyl acetate (20 mL)
  7. dry with materialThe combined organic layer was dried with Na2SO4
  8. concentrationconcentrated in vacuo
  9. custompurified by silica gel chromatography

出典と根拠

ORDレコード
ord-55f76d26021948b5b4db730e8061adb4
出典データセット
uspto-grants-2011_03
特許番号
US07897737B2

関連ノート

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