alpha-D-Glucopyranosyl bromide, tetraacetate → 4-[(4-Isopropoxy-phenyl)methyl]-5-methyl-3-(2,3,4,6-tetra-o-acetyl-beta-d-glucopyranosyloxy)-1h-pyrazole

HRID 7387

反応式

[CH:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]2[C:13](=[O:18])[NH:14][NH:15][C:16]=2[CH3:17])=[CH:7][CH:6]=1)([CH3:3])[CH3:2].[CH3:19][C:20]([O:22][CH2:23][C@H:24]1[O:29][C@H:28](Br)[C@H:27]([O:31][C:32]([CH3:34])=[O:33])[C@@H:26]([O:35][C:36]([CH3:38])=[O:37])[C@@H:25]1[O:39][C:40]([CH3:42])=[O:41])=[O:21]>O1CCCC1.C(=O)([O-])[O-].[Ag+2]>[CH:1]([O:4][C:5]1[CH:6]=[CH:7][C:8]([CH2:11][C:12]2[C:13]([O:18][C@@H:28]3[O:29][C@H:24]([CH2:23][O:22][C:20](=[O:21])[CH3:19])[C@@H:25]([O:39][C:40](=[O:41])[CH3:42])[C@H:26]([O:35][C:36](=[O:37])[CH3:38])[C@H:27]3[O:31][C:32](=[O:33])[CH3:34])=[N:14][NH:15][C:16]=2[CH3:17])=[CH:9][CH:10]=1)([CH3:3])[CH3:2]

参加物

反応条件

温度: 65 °C

実験手順

To a suspension of 4-[(4-isopropoxyphenyl)methyl]-5-methyl-1,2-dihydro-3H-pyrazol-3-one (46 mg), acetobromo-α-D-glucose (99 mg) and 4A molecular sieves in tetrahydrofuran (3 mL) was added silver carbonate (66 mg), and the mixture was stirred at 65° C. overnight under light shielding. The reaction mixture was purified by column chromatography on aminopropyl silica gel (eluent: tetrahydrofuran), and successively by preparative thin layer chromatography on silica gel (developing solvent: ethyl acetate/hexane=2/1) to give 4-[(4-isopropoxyphenyl)methyl]-5-methyl-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-1H-pyrazole (42 mg).

後処理

customThe reaction mixture was purified by column chromatography on aminopropyl silica gel (eluent: tetrahydrofuran)

出典と根拠

ORDレコード: ord-565d90381b814599892f25d706657501
出典データセット: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US07087579B2

反応式

参加物

反応物 2

生成物 1

試薬・触媒・溶媒 2

反応条件

実験手順

後処理

出典と根拠

関連ノート