Tetrabutylammonium Fluoride → HCID 86684713, compound

HRID 1057227Notes

Reaction equation

HRID 1057227 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[N+:39]([O-:41])=[O:40])[C:26]([NH2:27])=[N:25][C:23]2=[O:24])[CH2:9]1)(C(C)(C)C)(C)C.[N+](CCCC)(CCCC)(CCCC)CCCC.[F-]>C1COCC1>[N+: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]([NH2:27])=[N: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)([O-:41])=[O:40]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86684714HCID 86684714, compound

Product 1

HCID 86684713HCID 86684713, compoundYield 96.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of compound 42 (55 mg, 0.09 mmol) in THF (10 mL), n-Bu4NF (63 mg, 0.20 mmol) was added. The mixture was stirred at room temperature for four hours and concentrated in vacuo, and the residue was purified by silica gel column chromatography to yield 5-(2-nitrobenzyloxyl)methyl-2′-deoxycytidine 43 (34 mg, 96%). 1H NMR (400 MHz, DMSO-d6): δ 8.05 (d, J=8.0 Hz, 1H, Ph-H), 7.89 (s, 1H, H-6), 7.74 (m, 2H, Ph-H), 7.55 (m, 1H, Ph-H), 7.39 (br s, 1H, D2O exchangeable, NH2), 6.74 (br s, 1H, D2O exchangeable, NH2), 6.12 (t, 1H, J=6.4 Hz, H-1′), 5.21 (br s, 1H, D2O exchangeable, 3′-OH), 4.99 (br s, 1H, D2O exchangeable, 5′-OH), 4.81 (s, 2H, Ph-CH2), 4.30 (dd, 2H, J=11.6 Hz, 5-CH2), 4.20 (m, 1H, H-3′), 3.76 (m, 1H, H-4′), 3.55 (m, 2H, H-5′), 2.11 (m, 1H, H-2′a), 1.95 (m, 1H, H-2′b).

Workup

  1. concentrationconcentrated in vacuo
  2. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ae9a85ccda0044ff9c42b837950e3ac4
Source dataset
uspto-grants-2016_07
Patent number
US09399798B2

Reaction notes

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