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

HRID 355351

反応式

HRID 355351 の反応式
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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 82844Platinum oxide (PtO)触媒HCID 702Ethanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-eadfb03e7d9d4538bf9f530b7737807b
出典データセット
uspto-grants-1998_11
特許番号
US05830873

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