Sodium Thiosulfate → (3aR,4R,6R,6aR)-6-(6-Chloro-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-carbaldehyde

HRID 552705ノート

反応式

HRID 552705 の反応式
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[Cl:23][C:24]1[N:32]=[CH:31][N:30]=[C:29]2[C:25]=1[N:26]=[CH:27][N:28]2[C@H:33]1[C@@H:37]2[O:38][C:39]([CH3:42])([CH3:41])[O:40][C@@H:36]2[C@@H:35]([CH2:43][OH:44])[O:34]1.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)Cl.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>[Cl:23][C:24]1[N:32]=[CH:31][N:30]=[C:29]2[C:25]=1[N:26]=[CH:27][N:28]2[C@H:33]1[C@@H:37]2[O:38][C:39]([CH3:41])([CH3:42])[O:40][C@H:36]2[C@H:35]([CH:43]=[O:44])[O:34]1

参加物

6

反応物 3

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 117271506-Chloro-9-[2,3-O-(1-methylethylidene)-beta-D-ribofuranosyl]-9H-Purine

生成物 1

HCID 86607307(3aR,4R,6R,6aR)-6-(6-Chloro-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-carbaldehyde収率 86%

試薬・触媒・溶媒 2

HCID 159087Triacetoxyperiodinane触媒HCID 6344Dichloromethane溶媒2 回

実験手順

To a suspension of Dess-Martin periodinane (16.42 g, 0.03872 mol) in anhydrous methylene chloride (88.0 mL) cooled in an ice/water bath was added [(3aR,4R,6R,6aR)-6-(6-chloro-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]methanol (11.50 g, 0.03520 mol) in methylene chloride (200 mL). The reaction was stirred under an atmosphere of nitrogen and allowed to warm to ambient temperature. After 2 hours, a further portion of Dess-Martin periodinane (1.00 g, 0.00236 mol) was added. After 3 hours, a solution (200 mL) of sodium thiosulfate (50 g in 200 mL of saturated aqueous sodium bicarbonate) was added and the mixture stirred for 10 min. The aqueous was extracted 2×250 mL methylene chloride and 8×50 mL of chloroform. The combined organics were washed with water and dried over magnesium sulfate and concentrated in vacuo to dryness. The residue was taken up in dry toluene (200 mL) and concentrated in vacuo, and then taken up in dry methylene chloride and concentrated in vacuo to yield the product as a foam (9.83 g, 86%).

後処理

  1. temperaturecooled in an ice/water bath
  2. waitAfter 3 hours
  3. stirringthe mixture stirred for 10 min
  4. extractionThe aqueous was extracted 2×250 mL methylene chloride and 8×50 mL of chloroform
  5. washThe combined organics were washed with water
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo to dryness
  8. concentrationconcentrated in vacuo
  9. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-6df79687c84b4e14884c1c17a5ca154e
出典データセット
uspto-grants-2011_05
特許番号
US07951810B2

反応ノート

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