Trimethylsilyl triflate → HCID 89975769, compound

HRID 1508628Notes

Reaction equation

HRID 1508628 reaction equation
C/C(/O[Si](C)(C)C)=N\[Si](C)(C)C.C(O[C@@H:17]1[S:39][C@H:38]([CH2:40][O:41][C:42](=[O:49])[C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[C@@H:28]([O:29][C:30](=[O:37])[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C@H:18]1[O:19][C:20](=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(=O)C.[NH:50]1[CH:57]=[CH:56][C:54]([NH2:55])=[N:53][C:51]1=[O:52].FC(F)(F)S(O[Si](C)(C)C)(=O)=O>C(#N)C.C(OCC)(=O)C>[C:20]([O:19][C@@H:18]1[C@H:28]([O:29][C:30](=[O:37])[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[C@@H:38]([CH2:40][O:41][C:42](=[O:49])[C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=2)[S:39][C@H:17]1[N:50]1[CH:57]=[CH:56][C:54]([NH2:55])=[N:53][C:51]1=[O:52])(=[O:27])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

7

Reactant 4

HCID 65367Trimethylsilyl triflateHCID 6913588N,O-bis(trimethylsilyl)acetamideHCID 24851310HCID 24851310, compoundHCID 178418229Cytosine

Product 1

HCID 89975769HCID 89975769, compoundYield 30.6%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

0.44 mL of N,O-bis(trimethylsilyl)acetamide was added to a suspension of 208 mg of 1-O-acetyl-2,3,5-tri-O-benzoyl-4-thio-β-D-ribofuranose and 67 mg of cytosine in 2.0 mL of acetonitrile, and the obtained mixture was then stirred at 60° C. for 1 hour. Thereafter, 0.22 mL of trimethylsilyl trifluoromethanesulfonate was added to the reaction mixture, and the obtained mixture was then stirred at 80° C. for 4 hours. Thereafter, ethyl acetate was added to the reaction mixture, and the thus obtained mixture was then washed with a saturated sodium hydrogen carbonate aqueous solution. After that, the solvent was distilled away under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate/methanol=1/0 to 4/1), so as to obtain 70 mg of 1-(2,3,5-tri-O-benzoyl-4-thio-β-D-ribofuranosyl)cytosine in the form of a white solid.

Workup

  1. stirringthe obtained mixture was then stirred at 80° C. for 4 hours
  2. washthe thus obtained mixture was then washed with a saturated sodium hydrogen carbonate aqueous solution
  3. distillationAfter that, the solvent was distilled away under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate/methanol=1/0 to 4/1)

Sources & evidence

ORD record
ord-2c14c5b89e8f43a0a6d5e5978f02ccdc
Source dataset
uspto-grants-2015_12
Patent number
US09221865B2

Reaction notes

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