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

HRID 611802ノート

反応式

HRID 611802 の反応式
[CH:1](I)([CH3:3])[CH3:2].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>[CH:1]([O:8][C@@H:9]1[C@@H:14]([O:15][CH:16]([CH3:17])[CH3:22])[C@H:13]([CH3:19])[O:12][CH:11]=[CH:10]1)([CH3:3])[CH3:2]

参加物

6

反応物 4

HCID 679Dimethyl SulfoxideHCID 6362Isopropyl iodideHCID 14798Sodium HydroxideHCID 2734733L-arabino-Hex-1-enitol, 1,5-anhydro-2,6-dideoxy-, diacetate

生成物 1

HCID 183962693,4-Di-O-i-propyl-6-deoxy-L-glucal収率 28%

試薬・触媒・溶媒 1

HCID 94433Tetrabutylammonium hydrogen sulfate触媒

実験手順

i-Propyl iodide (40 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 67 h. at room temperature and for 24 h at reflux temperature. The mixture was cooled to room temperature and partitioned between water and pentane. The aqueous layer was extracted with additional pentane. The combined organic layers were successively washed with water (four times), dilute aqueous sodium thiosulfate, water, and saturated sodium bicarbonate. The solvent was removed under reduced pressure (20 Torr followed by 0.1 Torr) to yield a light yellow oil (1.2 g, 28%) that could be used without further purification. 1H NMR d 6.29 (dd, J=6.1, 1.4, 1 H), 4.70 (dd, J=6.1, 2.4, 1 H), 1.35 (d, J=6.4, 3 H), 1.21 (d, J=6.4, 3 H), 1.18 (d, J=6.4, 6 H), 1.17 (d, J=6.4, 3 H).

後処理

  1. customthree-neck flask equipped with an overhead stirrer
  2. stirringThe mixture was stirred for 67 h. at room temperature and for 24 h
  3. temperatureat reflux temperature
  4. custompartitioned between water and pentane
  5. extractionThe aqueous layer was extracted with additional pentane
  6. washThe combined organic layers were successively washed with water (four times), dilute aqueous sodium thiosulfate, water, and saturated sodium bicarbonate
  7. 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-2c38c4e6b32a4003aad83312f5a79e2b
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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