Thymidine → 5'-O-tert-Butyldimethylsilylthymidine

HRID 600109

反応式

HRID 600109 の反応式
[C@@H:1]1([N:9]2[CH:17]=[C:15]([CH3:16])[C:13](=[O:14])[NH:12][C:10]2=[O:11])[O:8][C@H:5]([CH2:6][OH:7])[C@@H:3]([OH:4])[CH2:2]1.[CH3:18][C:19]([Si:22](Cl)([CH3:24])[CH3:23])([CH3:21])[CH3:20]>C(Cl)Cl>[Si:22]([O:7][CH2:6][C@H:5]1[O:8][C@@H:1]([N:9]2[CH:17]=[C:15]([CH3:16])[C:13](=[O:14])[NH:12][C:10]2=[O:11])[CH2:2][C@@H:3]1[OH:4])([C:19]([CH3:21])([CH3:20])[CH3:18])([CH3:24])[CH3:23]

参加物

4

反応物 2

HCID 5789ThymidineHCID 28928tert-Butyldimethylsilyl chloride

生成物 1

HCID 102512595'-O-tert-Butyldimethylsilylthymidine

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of thymidine dT (2.85 g, 11.76 mmol), imidiazole (2.44 g, 35.80 mmol) and TBSCl (1.77 g, 11.76 mmol) in anhydrous CH2Cl2 (20 mL) was stirred at room temperature overnight under a N2 atmosphere. The reaction mixture was then concentrated in vacuo to a viscous oil, followed by the addition of ethyl ether (60 mL) and water (60 mL). The organic layer was separated and washed twice with water (20 mL each), and the combined aqueous layer was extracted with ethyl ether (20 mL). The combined organic layer was dried over Na2SO4, concentrated in vacuo and purified by silica gel column chromatography to give 5′-O-tert-butyldimethylsilyl-thymidine dT.01 (3.44 g, 82%) as a white solid.

後処理

  1. concentrationThe reaction mixture was then concentrated in vacuo to a viscous oil
  2. additionfollowed by the addition of ethyl ether (60 mL) and water (60 mL)
  3. customThe organic layer was separated
  4. washwashed twice with water (20 mL each)
  5. extractionthe combined aqueous layer was extracted with ethyl ether (20 mL)
  6. dry with materialThe combined organic layer was dried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. custompurified by silica gel column chromatography

出典と根拠

ORDレコード
ord-7e6114f3df0e4959a72434e1068ec6e6
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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