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

HRID 129889Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 129889
[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]

Komponenten

8

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 30318Osmium TetroxideKatalysatorHCID 180AcetoneLösungsmittelHCID 6386tert-ButanolLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-b74252f2fc6a4a72836500c50dd592cb
Quelldatensatz
uspto-grants-1995_11
Patentnummer
US05470878

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