3-Buten-1-ol → 4-{4-[(1E)-4-hydroxybut-1-en-1-yl]-2-methylbenzyl}-5-(propan-2-yl)-1H-pyrazol-3-yl 2,3,4,6-tetra-O-benzoyl-beta-D-glucopyranoside

HRID 931672ノート

反応式

HRID 931672 の反応式
[CH2:1]([OH:5])[CH2:2][CH:3]=[CH2:4].[C:6]([O:14][C@@H:15]1[C@@H:38]([O:39][C:40](=[O:47])[C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[C@H:37]([O:48][C:49](=[O:56])[C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[C@@H:36]([CH2:57][O:58][C:59](=[O:66])[C:60]2[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=2)[O:35][C@H:16]1[O:17][C:18]1[C:22]([CH2:23][C:24]2[CH:29]=[CH:28][C:27](Br)=[CH:26][C:25]=2[CH3:31])=[C:21]([CH:32]([CH3:34])[CH3:33])[NH:20][N:19]=1)(=[O:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C(#N)C.C(N(CC)CC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:6]([O:14][C@@H:15]1[C@@H:38]([O:39][C:40](=[O:47])[C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[C@H:37]([O:48][C:49](=[O:56])[C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[C@@H:36]([CH2:57][O:58][C:59](=[O:66])[C:60]2[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=2)[O:35][C@H:16]1[O:17][C:18]1[C:22]([CH2:23][C:24]2[CH:29]=[CH:28][C:27](/[CH:4]=[CH:3]/[CH2:2][CH2:1][OH:5])=[CH:26][C:25]=2[CH3:31])=[C:21]([CH:32]([CH3:34])[CH3:33])[NH:20][N:19]=1)(=[O:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

参加物

7

反応物 3

HCID 693893-Buten-1-olHCID 80271Tri-o-tolylphosphineHCID 867208784-(4-bromo-2-methylbenzyl)-5-(propan-2-yl)-1H-pyrazol-3-yl 2,3,4,6-tetra-O-benzoyl-beta-D-glucopyranoside

生成物 1

HCID 867208804-{4-[(1E)-4-hydroxybut-1-en-1-yl]-2-methylbenzyl}-5-(propan-2-yl)-1H-pyrazol-3-yl 2,3,4,6-tetra-O-benzoyl-beta-D-glucopyranoside収率 70.6%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 6342Acetonitrile溶媒HCID 8471Triethylamine溶媒

反応条件

温度
90 °C

実験手順

Add 3-buten-1-ol (0.58 mL, 6.8 mmol) to a solution of 4-(4-bromo-2-methylbenzyl)-5-(propan-2-yl)-1H-pyrazol-3-yl 2,3,4,6-tetra-O-benzoyl-beta-D-glucopyranoside (3 g, 3.4 mmol) in acetonitrile (30 mL) and triethylamine (20 mL). Degas the solution with nitrogen over 10 minutes. Add tri-o-tolylphosphine (205 mg, 0.67 mmol) and palladium acetate (76 mg, 0.34 mmol). Reflux at 90° C. for 2 hours. Cool to room temperature and concentrate to remove the solvent under the reduced pressure. Purify the residue by flash chromatography to yield the title compound (2.1 g, 2.4 mmol). MS (m/z): 878.4 (M+1).

後処理

  1. customDegas the solution with nitrogen over 10 minutes
  2. temperatureCool to room temperature
  3. concentrationconcentrate
  4. customto remove the solvent under the reduced pressure
  5. customPurify the residue by flash chromatography

出典と根拠

ORDレコード
ord-7407444acdb54ce891ade3a235d73ec4
出典データセット
uspto-grants-2016_03
特許番号
US09296775B2

反応ノート

読み込み中…