Tetrabutylammonium Fluoride → 2'-Deoxy-5-ethynyl-5'-O-[(4-methoxyphenyl)(diphenyl)methyl]uridine

HRID 1816513Notes

Reaction equation

HRID 1816513 reaction equation
C[Si]([C:5]#[C:6][C:7]1[C:8](=[O:43])[NH:9][C:10](=[O:42])[N:11]([CH:41]=1)[C@@H:12]1[O:40][C@H:16]([CH2:17][O:18][C:19]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)[C@@H:14]([OH:15])[CH2:13]1)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[C:6]([C:7]1[C:8](=[O:43])[NH:9][C:10](=[O:42])[N:11]([CH:41]=1)[C@@H:12]1[O:40][C@H:16]([CH2:17][O:18][C:19]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:20]2[CH:21]=[CH:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=2)[C@@H:14]([OH:15])[CH2:13]1)#[CH:5]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 20778052HCID 20778052, compound

Product 1

HCID 186671312'-Deoxy-5-ethynyl-5'-O-[(4-methoxyphenyl)(diphenyl)methyl]uridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.40 g of 2′-deoxy-5-[(trimethylsilyl)ethynyl]-5′-O-(4-methoxytrityl)-uridine (2.35 mmole) prepared in 1-2) was dissolved in 20 ml of THF, and then 0.95 ml TBAF (1.4 eq) was added thereto. After 7 hours, the reaction was terminated, THF was removed using a rotary evaporator, and the resulting residue was subjected to column chromatography (silica gel 60, 230-400 meshes, Merck) to obtain the title compound as a solid. The chromatography was conducted using a mixture of CH2Cl2 and methanol as an eluting solution whose mix ratio was gradually varied from 100:1 to 50:1 (v/v).

Workup

  1. customthe reaction was terminated
  2. customTHF was removed
  3. customa rotary evaporator

Sources & evidence

ORD record
ord-b4fc1b580c7343b0a205a7edf04d57d6
Source dataset
uspto-grants-2005_04
Patent number
US06884882B1

Reaction notes

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