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

HRID 611802노트

반응식

HRID 611802 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 94433Tetrabutylammonium hydrogen sulfate촉매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-2c38c4e6b32a4003aad83312f5a79e2b
출처 데이터셋
uspto-grants-1999_12
특허 번호
US06001981

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