(S)-beta-Benzoyloxy-gamma-butyrolactone → 3-O-benzoyl-2-deoxy-threose

HRID 1886880

반응식

HRID 1886880 반응식
[C:1]([O:9][C@@H:10]1[CH2:15][O:14][C:12](=[O:13])[CH2:11]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].C([Al+]C(C)C)(C)C>C1COCC1.C1(C)C=CC=CC=1>[C:1]([O:9][C@H:10]([CH2:15][OH:14])[CH2:11][CH:12]=[O:13])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

5

반응물 2

HCID 10058799(S)-beta-Benzoyloxy-gamma-butyrolactoneHCID 21896610Diisopropylaluminium hydride

생성물 1

HCID 866645133-O-benzoyl-2-deoxy-threose수율 75%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

To a solution of 101 (0.780 g, 3.8 mmol) in 13 mL dry THF was slowly dropwise added 1.0 M diisopropyl aluminiumhydride (4.7 mL, 4.7 mmol) in toluene at −78° C. The reaction mixture was stirred at −78° C., and as soon as the starting material was completely consumed (TLC, 2 hours), methanol (2 mL) was slowly added in order to quench the reaction. The cooling bath was removed, 15 mL of a saturated aqueous sodium potassium tartrate solution and 25 mL of EtOAc were added and the mixture stirred vigorously for 3 hours. The organic layer was washed with water and brine, and concentrated under vacuo. The residue was purified by chromatography on a silica gel column (n-hexane/EtOAc=8:2) to afford 102 (590 mg, 2.8 mmol) as a colorless oil, in 75% yield, which was characterized as follows:

후처리

  1. customat −78° C
  2. customas soon as the starting material was completely consumed (TLC, 2 hours), methanol (2 mL)
  3. additionwas slowly added in order
  4. customto quench
  5. customthe reaction
  6. customThe cooling bath was removed
  7. addition15 mL of a saturated aqueous sodium potassium tartrate solution and 25 mL of EtOAc were added
  8. stirringthe mixture stirred vigorously for 3 hours
  9. washThe organic layer was washed with water and brine
  10. concentrationconcentrated under vacuo
  11. customThe residue was purified by chromatography on a silica gel column (n-hexane/EtOAc=8:2)

출처 및 근거

ORD 기록
ord-a2ca14c10a9743c0adbbcee7b1543bc2
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08501709B2

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