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

HRID 355351

반응식

HRID 355351 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+]>C(O)C.[Pt]=O>[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])[CH:33]=[CH: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

6

반응물 3

HCID 14797Potassium HydroxideHCID 27738751-Benzofuran-5-carbaldehydeHCID 541762952'-(2,3,4,6-Tetra-O-acetyl-alpha-D-glucopyranosyloxy)-6'-hydroxyacetophenone

생성물 1

HCID 675662482'-(beta-D-glucopyranosyloxy)-6'-hydroxy-3-(5-benzo[b]furanyl)acrylophenone

시약·촉매·용매 2

HCID 82844Platinum oxide (PtO)촉매HCID 702Ethanol용매

실험 절차

2'-(2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyloxy)-6'-hydroxyacetophenone (5 g) and benzo[b]furan-5-carbaldehyde (1.81 g) are (i) treated in the same manner as in Example 1 to give crude 2'-(β-D-glucopyranosyloxy)-6'-hydroxy-3-(5-benzo[b]furanyl)acrylophenone, which is dissolved in a mixture of ethanol (50 ml) and a 10% aqueous potassium hydroxide solution (10 ml). The mixture is subjected to catalytic hydrogenation by using as a catalyst platinum oxide (120 mg) under atmospheric pressure. The catalyst is removed by filtration, and the filtrate is neutralized with a 10% hydrochloric acid under ice-cooling, and concentrated under reduced pressure. To the residue is added ethyl acetate, and the mixture is stirred, and the organic layer is collected; (ii) treated in the same manner as in Example 1 to give crude 2'-(β-D-glucopyranosyloxy)-6'-hydroxy-3-(5-benzo[b]furanyl)acrylophenone, which is dissolved in a mixture of ethanol (50 ml) and a 10% aqueous potassium hydroxide solution (10 ml). To the solution is added 4-N,N-diemethylaminopyridine (2.5 g) and the mixture is subjected to catalytic hydrogenation by using as a catalyst 10% palladium-carbon (1.1 g) under atmospheric pressure. The catalyst is removed by filtration, and the filtrate is neutralized with a 10% hydrochloric acid under ice-cooling, and concentrated under reduced pressure. To the residue is added ethyl acetate, and the mixture is stirred, and the organic layer is collected; or (iii) treated in the same manner as in Example 2, and the organic layer is collected.

후처리

  1. additiontreated in the same manner as in Example 1
  2. customto give crude 2'-(β-D-glucopyranosyloxy)-6'-hydroxy-3-(5-benzo[b]furanyl)acrylophenone, which
  3. customThe catalyst is removed by filtration
  4. temperaturecooling
  5. concentrationconcentrated under reduced pressure
  6. additionTo the residue is added ethyl acetate
  7. customthe organic layer is collected
  8. addition(ii) treated in the same manner as in Example 1

출처 및 근거

ORD 기록
ord-eadfb03e7d9d4538bf9f530b7737807b
출처 데이터셋
uspto-grants-1998_11
특허 번호
US05830873

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