5'-O-t-Butyldiphenylsilyl-3-benzyloxymethyl-2'-O-(methoxyethyl)-5-methyluridine → 5'-O-t-Butyldiphenylsilyl-2'-O-(methoxyethyl)-5-methyluridine

HRID 2186435Notes

Reaction equation

HRID 2186435 reaction equation
[Si:1]([O:18][CH2:19][C@H:20]1[O:24][C@@H:23]([N:25]2[CH:32]=[C:31]([CH3:33])[C:29](=[O:30])[N:28](COCC3C=CC=CC=3)[C:26]2=[O:27])[C@H:22]([O:43][CH2:44][CH2:45][O:46][CH3:47])[C@@H:21]1[OH:48])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>CO.[Pd]>[Si:1]([O:18][CH2:19][C@H:20]1[O:24][C@@H:23]([N:25]2[CH:32]=[C:31]([CH3:33])[C:29](=[O:30])[NH:28][C:26]2=[O:27])[C@H:22]([O:43][CH2:44][CH2:45][O:46][CH3:47])[C@@H:21]1[OH:48])([C:14]([CH3:16])([CH3:15])[CH3:17])([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 213484865'-O-t-Butyldiphenylsilyl-3-benzyloxymethyl-2'-O-(methoxyethyl)-5-methyluridineHCID 178418361HCID 178418361, compound

Product 1

HCID 213484835'-O-t-Butyldiphenylsilyl-2'-O-(methoxyethyl)-5-methyluridine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

5′-O-t-Butyldiphenylsilyl-3-benzyloxymethyl-2′-O-(methoxyethyl)-5-methyluridine is dissolved in anhydrous MeOH and is added to a pressure bottle containing 10% Pd on carbon under an argon atmosphere. The vessel is pressurized with hydrogen gas to 30 psi and shaken for 16 hours. The mixture is filtered through a celite pad and the solvent is evaporated in vacuo. The residue is dissolved in 1M NEt3in anhydrous MeOH and the solution is heated at reflux temperature for 2 hours. The solvent is evaporated in vacuo to give the title compound.

Workup

  1. additionis added to a pressure bottle
  2. filtrationThe mixture is filtered through a celite pad
  3. customthe solvent is evaporated in vacuo
  4. dissolutionThe residue is dissolved in 1M NEt3in anhydrous MeOH
  5. temperaturethe solution is heated
  6. temperatureat reflux temperature for 2 hours
  7. customThe solvent is evaporated in vacuo

Sources & evidence

ORD record
ord-87a1ba0b3edf4704a7b52ffb1d912b7c
Source dataset
uspto-grants-2002_06
Patent number
US06403779B1

Reaction notes

Loading…