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

HRID 129889ノート

反応式

HRID 129889 の反応式
[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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 30318Osmium Tetroxide触媒HCID 180Acetone溶媒HCID 6386tert-Butanol溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-b74252f2fc6a4a72836500c50dd592cb
出典データセット
uspto-grants-1995_11
特許番号
US05470878

反応ノート

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