Methyl morpholine oxide → HCID 22872315, compound

HRID 55554Notes

Reaction equation

HRID 55554 reaction equation
[Si:1]([O:8][CH2:9][C@H:10]1[O:14][C@@H:13]([N:15]2[CH:23]=[C:21]([CH3:22])[C:19](=[O:20])[NH:18][C:16]2=[O:17])[CH2:12][C@@H:11]1[C:24](=[O:29])C=CCC)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C[N+]1([O-])CCOCC1.I([O-])(=O)(=O)=O.[Na+].S(=O)(O)[O-].[Na+]>CC(C)=O.O.[Os](=O)(=O)(=O)=O>[Si:1]([O:8][CH2:9][C@H:10]1[O:14][C@@H:13]([N:15]2[CH:23]=[C:21]([CH3:22])[C:19](=[O:20])[NH:18][C:16]2=[O:17])[CH2:12][C@@H:11]1[CH:24]=[O:29])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 82029Methyl morpholine oxideHCID 23665763Sodium BisulfiteHCID 23667635Sodium periodateHCID 131720002HCID 131720002, compound

Product 1

HCID 22872315HCID 22872315, compoundYield 69.6%

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

5'-O-tert-Butyldimethylsilyl-3'-deoxy-3'-formylthymidine (Compound 11, Table VII) was prepared by dissolving 5'-O-tert-Butyldimethylsilyl-3'-deoxy-3'-ethylacrylylthymidine (1 g, 2.3 mmole) and 4-methylmorpholine-N-oxide (0.52 g, 4.4 mmole) in a solution of 40 ml acetone and 4 ml water to give a clear pale yellow solution. Aqueous osmium tetroxide (11.2 ml, 0.050 g/ml, 2.2 mmole) was then added and the resulting pale yellow mixture stirred for 2 hours. After this time 1.17 g sodium periodate (5.47 mmole) was added to the reaction and stirring was continued for one more hour. The stirred mixture was then treated with 0.60 g sodium bisulfite and the reaction stirred for an additional hour. At this time the solvent was evaporated and the residue was redissolved in 30 ml ethyl acetate. The solution containing the redissolved residue was washed with water (3×20 ml) and then dried over anhydrous sodium sulfate. Evaporation of the solvent yielded 0.59 g 5'-O-tert-butyldimethylsilyl-3'-deoxy-3'-formylthymidine as a crude red foam that was generally used without further purification (71% yield).

Workup

  1. custom5'-O-tert-Butyldimethylsilyl-3'-deoxy-3'-formylthymidine (Compound 11, Table VII) was prepared
  2. customto give a clear pale yellow solution
  3. stirringstirring
  4. stirringthe reaction stirred for an additional hour
  5. customAt this time the solvent was evaporated
  6. dissolutionthe residue was redissolved in 30 ml ethyl acetate
  7. additionThe solution containing the redissolved residue
  8. washwas washed with water (3×20 ml)
  9. dry with materialdried over anhydrous sodium sulfate
  10. customEvaporation of the solvent

Sources & evidence

ORD record
ord-f563f3ce8ab14db987a228e7f3602e99
Source dataset
uspto-grants-1997_04
Patent number
US05625050

Reaction notes

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