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

HRID 129889노트

반응식

HRID 129889 반응식
[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]

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 30318Osmium Tetroxide촉매HCID 180Acetone용매HCID 6386tert-Butanol용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-b74252f2fc6a4a72836500c50dd592cb
출처 데이터셋
uspto-grants-1995_11
특허 번호
US05470878

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