Tetrabutylammonium Fluoride → HCID 86684713, compound

HRID 339211Notes

Reaction equation

HRID 339211 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-nitrobenzyloxy)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-6944f05910ff4cd7b9255449c83dc03e
Source dataset
uspto-grants-2014_11
Patent number
US08889860B2

Reaction notes

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