Thymidine → 5'-O-tert-Butyldimethylsilylthymidine

HRID 871789Notes

Reaction equation

HRID 871789 reaction equation
[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]

Participants

4

Reactant 2

HCID 5789ThymidineHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 102512595'-O-tert-Butyldimethylsilylthymidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-e6215dbd9e464969a88c37a4b6c44360
Source dataset
uspto-grants-2015_03
Patent number
US08969535B2

Reaction notes

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