Thymidine → 5'-O-tert-Butyldimethylsilylthymidine

HRID 600109

Reaktionsgleichung

Reaktionsgleichung von HRID 600109
[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]

Komponenten

4

Edukt 2

HCID 5789ThymidineHCID 28928tert-Butyldimethylsilyl chloride

Produkt 1

HCID 102512595'-O-tert-Butyldimethylsilylthymidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-7e6114f3df0e4959a72434e1068ec6e6
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07897737B2

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