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Thymidine → 5'-O-(4,4'-di-3,5-hexadienoxytrityl)thymidine

HRID 611750
Notes
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Reaction equation

HRID 611750 reaction equation
[CH2:1]([O:7][C:8]1[CH:34]=[CH:33][C:11]([C:12]([OH:32])([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][CH:22]=[CH:23][CH:24]=[CH2:25])=[CH:15][CH:14]=2)=[CH:10][CH:9]=1)[CH2:2][CH:3]=[CH:4][CH:5]=[CH2:6].C(Cl)(=O)C.[C@@H:39]1([N:47]2[CH:55]=[C:53]([CH3:54])[C:51](=[O:52])[NH:50][C:48]2=[O:49])[O:46][C@H:43]([CH2:44]O)[C@@H:41]([OH:42])[CH2:40]1.CN(C1N=CC=CN=1)C>C1(C)C=CC=CC=1.N1C=CC=CC=1>[CH2:1]([O:7][C:8]1[CH:34]=[CH:33][C:11]([C:12]([O:32][CH2:44][C@H:43]2[O:46][C@@H:39]([N:47]3[CH:55]=[C:53]([CH3:54])[C:51](=[O:52])[NH:50][C:48]3=[O:49])[CH2:40][C@@H:41]2[OH:42])([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][CH:22]=[CH:23][CH:24]=[CH2:25])=[CH:15][CH:14]=2)=[CH:10][CH:9]=1)[CH2:2][CH:3]=[CH:4][CH:5]=[CH2:6]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 5789ThymidineHCID 6367Acetyl chlorideHCID 5217172-DimethylaminopyrimidineHCID 538662944,4'-Di-3,5-hexadienoxytrityl alcohol

Product 1

HCID 538107565'-O-(4,4'-di-3,5-hexadienoxytrityl)thymidineYield 84.4%

Reagents, catalysts & solvents 2

HCID 1049
Pyridine
Solvent
2×
HCID 1140TolueneSolvent2×

Procedure

Compound 30 (3.5 grams, 7.73 mmol) was coevaporated with toluene (2×) and then dissolved in anhydrous toluene (85 mL). Acetyl chloride (33 mL, 464 mmol) was added to the solution and the reaction mixture was heated to reflux and stirred under argon. After 4 hours the reaction mixture was concentrated in vacuo and the crude product was coevaporated with pyridine and then dissolved in anhydrous pyridine (42 mL). Thymidine (1.5 grams, 6.18 mmol), which had been coevaporated with pyridine and dissolved in anhydrous pyridine (42 mL), was then added to the solution containing the crude product. A catalytic amount of dimethylaminopyrimidine (DMAP) was added and the reaction mixture was stirred under argon overnight and the solvent was evaporated. The residue was redissolved in dichloromethane and washed with a 5% aqueous solution of sodium bicarbonate followed by water. The organic phase was dried (MgSO4), evaporated and purified by column chromatography (silica gel; EtOAc/hexane, 1/1) to afford 3.53 grams (84%) of compound 31 as an off-white solid. 1H NMR (300 MHz, CDCl3) δ 1.47 (s, 3H), 2.22-2.46 (m, 2H), 2.50-2.63 (m, 4H), 3.35-3.58 (m, 2H), 3.85-4.09 (m, 5H), 4.51-4.60 (m, 1H), 5.02 (dd, J=1.5, 10.4 Hz, 2H), 5.14 (dd, J=1.5, 17.3 Hz, 2H), 5.68-5.83 (m, 2H), 6.12-6.45 (m, 5H), 6.82 (d, J=9.0 Hz, 4H), 7.18-7.46 (m, 9H), 7.58 (s, 1H), 8.44 (s, 1H); Anal. Calcd for C41H44N2O7.2H2O (712.8384): C, 69.08; H, 6.79; H, 3.93. Found: C, 69.34; H, 6.44; N, 3.91.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux
  3. concentrationAfter 4 hours the reaction mixture was concentrated in vacuo
  4. dissolutiondissolved in anhydrous pyridine (42 mL)
  5. additionwas then added to the solution
  6. stirringthe reaction mixture was stirred under argon overnight
  7. customthe solvent was evaporated
  8. dissolutionThe residue was redissolved in dichloromethane
  9. washwashed with a 5% aqueous solution of sodium bicarbonate
  10. dry with materialThe organic phase was dried (MgSO4)
  11. customevaporated
  12. custompurified by column chromatography (silica gel; EtOAc/hexane, 1/1)

Sources & evidence

ORD record
ord-bd8bd48f29f34f0b92b0d61285effb40
Source dataset
uspto-grants-1999_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06001966

Reaction notes

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