TBAF tetrahydrofuran → HCID 54112621, compound

HRID 1508627Notes

Reaction equation

HRID 1508627 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1.[Si]([O:41][C@@H:42]1[C@@H:46]([CH2:47][O:48][Si](C(C)(C)C)(C2C=CC=CC=2)C2C=CC=CC=2)[S:45][CH:44]([N:66]2[CH:73]=[CH:72][C:70]([NH2:71])=[N:69][C:67]2=[O:68])[C@H:43]1[F:74])(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1>O1CCCC1>[F:74][C@H:43]1[C@H:42]([OH:41])[C@@H:46]([CH2:47][OH:48])[S:45][CH:44]1[N:66]1[CH:73]=[CH:72][C:70]([NH2:71])=[N:69][C:67]1=[O:68]

Participants

4

Reactant 2

HCID 11078149TBAF tetrahydrofuranHCID 89975701HCID 89975701, compound

Product 1

HCID 54112621HCID 54112621, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.24 mL of 0.1 mol/L tetrabutyl ammonium fluoride/tetrahydrofuran solution was added to a solution of 43 mg of ((3S,4S,5R)-4-((tert-butyldiphenylsilyl)oxy)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-3-fluorotetrahydrothiophen-2-yl)cytosine in 1.0 mL of tetrahydrofuran. The obtained mixture was stirred at room temperature for 2 hours, and was then left overnight. Thereafter, the solvent was distilled away under reduced pressure, and the obtained residue was then purified by silica gel column chromatography (ethyl acetate/methanol=1/0 to 2/1), so as to obtain 14 mg of 1-(2-deoxy-2-fluoro-4-thio-D-arabinofuranosyl)cytosine in the form of a white solid.

Workup

  1. waitwas then left overnight
  2. distillationThereafter, the solvent was distilled away under reduced pressure
  3. customthe obtained residue was then purified by silica gel column chromatography (ethyl acetate/methanol=1/0 to 2/1)

Sources & evidence

ORD record
ord-a3cbe21179fd4b64b8fcc78e484eb61b
Source dataset
uspto-grants-2015_12
Patent number
US09221865B2

Reaction notes

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