Thymidine → 5'-O-tert-Butyldimethylsilylthymidine

HRID 1811374Notes

Reaction equation

HRID 1811374 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-c1dbc0d3bfb541988808ea9ef8de9bc8
Source dataset
uspto-grants-2013_01
Patent number
US08361727B2

Reaction notes

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