Water → 3-(5,6-Dihydroxyhexyl)-1-methylthymine

HRID 1955980Notes

Reaction equation

HRID 1955980 reaction equation
[CH2:1]([N:7]1[C:12](=[O:13])[C:11]([CH3:14])=[CH:10][N:9]([CH3:15])[C:8]1=[O:16])[CH2:2][CH2:3][CH2:4][CH:5]=[CH2:6].C[N+]1([O-])CC[O:21]CC1.[OH2:25].S(S([O-])=O)([O-])=O.[Na+].[Na+]>C(O)(C)(C)C.CC(C)=O.[Os](=O)(=O)(=O)=O>[OH:25][CH:5]([CH2:6][OH:21])[CH2:4][CH2:3][CH2:2][CH2:1][N:7]1[C:12](=[O:13])[C:11]([CH3:14])=[CH:10][N:9]([CH3:15])[C:8]1=[O:16]

Participants

8

Reactant 4

HCID 962WaterHCID 24489Sodium DithioniteHCID 82029Methyl morpholine oxideHCID 232959493-(5-Hexenyl)-1-methylthymine

Product 1

HCID 232879373-(5,6-Dihydroxyhexyl)-1-methylthymineYield 89%

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 180AcetoneSolventHCID 6386tert-ButanolSolvent

Procedure

A solution of 3-(5-hexenyl)-1-methylthymine (2.00 g, 9 mmol), 4-methylmorpholine-N-oxide (1.17 mg, 10 mmol), and osmium tetroxide (0.15 ml of a 2.5% solution in t-butanol) in acetone (15 ml) and water (10 ml) was stirred for 20 hours. Saturated aqueous sodium hydrosulfite solution (10 ml) was added and after 15 minutes of stirring, the mixture was extracted with 20% ethanol-dichloromethane (4×40 ml). The combined organic layers were dried over sodium sulfate and the solvents were evaporated under vacuum to give a solid residue. The solid was recrystallized (ethanol) to give 3-(5,6-dihydroxyhexyl)-1-methylthymine (2.00 g, 89% yield).

Workup

  1. extractionthe mixture was extracted with 20% ethanol-dichloromethane (4×40 ml)
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. customthe solvents were evaporated under vacuum
  4. customto give a solid residue
  5. customThe solid was recrystallized (ethanol)

Sources & evidence

ORD record
ord-ed02822606ab469283002c32a728576e
Source dataset
uspto-grants-1998_07
Patent number
US05777117

Reaction notes

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