Dimethyl Sulfoxide → 3,4-Di-O-n-propyl-6-deoxy-L-glucal

HRID 611801ノート

反応式

HRID 611801 の反応式
[CH2:1](I)[CH2:2][CH3:3].C([O:8][C@@H:9]1[C@@H:14]([O:15][C:16](=O)[CH3:17])[C@H:13]([CH3:19])[O:12][CH:11]=[CH:10]1)(=O)C.[OH-].[Na+].[CH3:22]S(C)=O>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:1]([O:8][C@@H:9]1[C@@H:14]([O:15][CH2:16][CH2:17][CH3:22])[C@H:13]([CH3:19])[O:12][CH:11]=[CH:10]1)[CH2:2][CH3:3]

参加物

6

反応物 4

HCID 679Dimethyl SulfoxideHCID 14798Sodium HydroxideHCID 336431-IodopropaneHCID 2734733L-arabino-Hex-1-enitol, 1,5-anhydro-2,6-dideoxy-, diacetate

生成物 1

HCID 183962703,4-Di-O-n-propyl-6-deoxy-L-glucal収率 94%

試薬・触媒・溶媒 1

HCID 94433Tetrabutylammonium hydrogen sulfate触媒

実験手順

n-Propyl iodide (39 mL, 0.40 mol), 3,4-di-O-acetyl-6-deoxy-L-glucal (4.28 g, 0.20 mol), 50% aqueous NaOH (43 mL, 0.81 mol) and DMSO (11.4 mL, 0.16 mol) were added sequentially to a 300-mL round-bottom, three-neck flask equipped with an overhead stirrer. Stirring was begun and tetrabutylammonium hydrogen sulfate (2.04 g, 0.006 mol) added in a single portion. The mixture was stirred for 17 h. at room temperature. The mixture was partitioned between water and pentane. The aqueous layer was extracted with additional pentane. The combined organic layers were successively washed with water (three times), dilute aqueous sodium thiosulfate, dilute sodium bicarbonate and brine. The solvent was removed under reduced pressure (20 Torr followed by 0.1 Torr) to yield a pale yellow oil (4.0 g, 94%) that could be used without further purification. 1H NMR d 6.31 (dd, J=6.1, 1.4, 1 H), 4.78 (dd, J=6.1, 2.4, 1 H), 1.60 (m, 4 H), 1.37 (d, J=6.4, 3 H), 0.93 (t, J=6.3, 3 H), 0.94 (t, J=6.3, 3 H).

後処理

  1. customthree-neck flask equipped with an overhead stirrer
  2. stirringThe mixture was stirred for 17 h. at room temperature
  3. customThe mixture was partitioned between water and pentane
  4. extractionThe aqueous layer was extracted with additional pentane
  5. washThe combined organic layers were successively washed with water (three times), dilute aqueous sodium thiosulfate, dilute sodium bicarbonate and brine
  6. customThe solvent was removed under reduced pressure (20 Torr followed by 0.1 Torr)

出典と根拠

ORDレコード
ord-a29df110581d42ba8fcbcab20801f2db
出典データセット
uspto-grants-1999_12
特許番号
US06001981

反応ノート

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