Potassium Hydroxide → 2'-(beta-D-glucopyranosyloxy)-6'-hydroxy-3-(5-benzo[b]furanyl)propiophenone

HRID 355343

반응식

HRID 355343 반응식
C([O:4][C@@H:5]1[C@@H:10]([O:11]C(=O)C)[C@H:9]([O:15]C(=O)C)[C@@H:8]([CH2:19][O:20]C(=O)C)[O:7][C@H:6]1[O:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([OH:31])[C:26]=1[C:32](=[O:34])[CH3:33])(=O)C.[O:35]1[CH:39]=[CH:38][C:37]2[CH:40]=[C:41]([CH:44]=O)[CH:42]=[CH:43][C:36]1=2.[OH-].[K+].[TeH2].[Na].[Te].[BH4-].[Na+]>C(O)C>[C@@H:6]1([O:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([OH:31])[C:26]=2[C:32](=[O:34])[CH2:33][CH2:44][C:41]2[CH:42]=[CH:43][C:36]3[O:35][CH:39]=[CH:38][C:37]=3[CH:40]=2)[O:7][C@H:8]([CH2:19][OH:20])[C@@H:9]([OH:15])[C@H:10]([OH:11])[C@H:5]1[OH:4]

참가 물질

8

반응물 6

HCID 14797Potassium HydroxideHCID 27738751-Benzofuran-5-carbaldehydeHCID 4311764Sodium borohydrideHCID 6327182TelluriumHCID 105527942'-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyloxy)-6'-hydroxyacetophenoneHCID 131720910Sodium tellurium hydride

생성물 1

HCID 99331252'-(beta-D-glucopyranosyloxy)-6'-hydroxy-3-(5-benzo[b]furanyl)propiophenone수율 54%

시약·촉매·용매 1

HCID 702Ethanol용매2회

실험 절차

To a mixture of 2'-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-6'-hydroxyacetophenone (965 mg), benzo[b]furan-5-carbaldehyde (350 mg) and ethanol (10 ml) is added dropwise a 50% aqueous potassium hydroxide solution (2 ml), and the mixture is stirred at room temperature overnight. The mixture is evaporated to remove the solvent, and to the residue are added water and diisopropyl ether. The mixture is stirred, and the aqueous layer is collected. The aqueous layer is neutralized with a 10% hydrochloric acid under ice-cooling, and extracted with ethyl acetate. The resulting organic layer is washed with water, dried, and evaporated to remove the solvent to give crude 2'-(β-D-glucopyranosyloxy)-6'-hydroxy-3-(5-benzo[b]furanyl)acrylophenone. This product is added to a solution of sodium tellurium hydride in ethanol (15 ml), which is previously prepared from tellurium (383 mg) and sodium borohydride (270 mg), and the mixture is reacted at room temperature for 2.5 hours. The insoluble materials are removed by filtration, and to the filtrate are added water and ethyl acetate. The mixture is stirred, and the organic layer is collected, washed with water, dried, and evaporated to remove the solvent. The residue is purified by silica gel column chromatography to give 2'-(β-D-glucopyranosyloxy)-6'-hydroxy-3-(5-benzo[b]furanyl)propiophenone (480 mg).

후처리

  1. customThe mixture is evaporated
  2. customto remove the solvent
  3. additionto the residue are added water and diisopropyl ether
  4. stirringThe mixture is stirred
  5. customthe aqueous layer is collected
  6. temperaturecooling
  7. extractionextracted with ethyl acetate
  8. washThe resulting organic layer is washed with water
  9. customdried
  10. customevaporated
  11. customto remove the solvent
  12. customto give crude 2'-(β-D-glucopyranosyloxy)-6'-hydroxy-3-(5-benzo[b]furanyl)acrylophenone
  13. customthe mixture is reacted at room temperature for 2.5 hours
  14. customThe insoluble materials are removed by filtration
  15. additionto the filtrate are added water and ethyl acetate
  16. stirringThe mixture is stirred
  17. customthe organic layer is collected
  18. washwashed with water
  19. customdried
  20. customevaporated
  21. customto remove the solvent
  22. customThe residue is purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-b95d04ede3654cd8ba5b5588accde24e
출처 데이터셋
uspto-grants-1998_11
특허 번호
US05830873

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