Tetrabutylammonium Fluoride Trihydrate → HCID 67113539, compound

HRID 1686877Notes

Reaction equation

HRID 1686877 reaction equation
[Si]([C@@:8]1([OH:42])[C@@H:12]([CH2:13][O:14][Si](C(C)(C)C)(C)C)[O:11][C@@H:10]([N:22]2[CH:29]=[C:28]([CH2:30][O:31][CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=3[CH:39]([CH3:41])[CH3:40])[C:26](=[O:27])[NH:25][C:23]2=[O:24])[CH2:9]1)(C(C)(C)C)(C)C.O.O.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH:39]([C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=1[CH2:32][O:31][CH2:30][C:28]1[C:26](=[O:27])[NH:25][C:23](=[O:24])[N:22]([CH:29]=1)[C@@H:10]1[O:11][C@H:12]([CH2:13][OH:14])[C@@H:8]([OH:42])[CH2:9]1)([CH3:41])[CH3:40]

Participants

4

Reactant 2

HCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 67113498HCID 67113498, compound

Product 1

HCID 67113539HCID 67113539, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Compounds 3′,5′-O-bis-(tert-butyldimethylsilyl)-5-(2-isopropylbenzyl-oxy)methyl-2′-deoxyuridine (134 mg, 0.22 mmol) and (3′ or 5′)-O-(tert-butyldimethylsilyl)-5-(2-isopropylbenzyloxy)methyl-2′-deoxyuridine (98 mg, 0.19 mmol) were dissolved in THF (5 mL), and a solution of tetra-n-butylammonium fluoride trihydrate (323 mg, 1.05 mmol) in THF (2 mL) was added. The mixture was stirred at room temperature for one hour, then concentrated in vacuo and purified by silica gel column chromatography to give 5-(2-isopropylbenzyloxy)methyl-2′-deoxyuridine dU.n6 (108 mg, 67%).

Workup

  1. concentrationconcentrated in vacuo
  2. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-15d4c3c3e6aa43a0a070449d16020fbe
Source dataset
uspto-grants-2012_04
Patent number
US08148503B2

Reaction notes

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