alpha-D-Glucopyranosyl bromide, tetraacetate → 4-((4-ethylthiophenyl)methyl]-5-methyl-3-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyloxy)-1H-pyrazole

HRID 6655

反応式

HRID 6655 の反応式
[CH2:1]([S:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]2[C:12](=[O:17])[NH:13][NH:14][C:15]=2[CH3:16])=[CH:6][CH:5]=1)[CH3:2].[CH3:18][C:19]([O:21][CH2:22][C@H:23]1[O:28][C@H:27](Br)[C@H:26]([O:30][C:31]([CH3:33])=[O:32])[C@@H:25]([O:34][C:35]([CH3:37])=[O:36])[C@@H:24]1[O:38][C:39]([CH3:41])=[O:40])=[O:20]>O1CCCC1.C(=O)([O-])[O-].[Ag+2]>[CH2:1]([S:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:10][C:11]2[C:12]([O:17][C@@H:27]3[O:28][C@H:23]([CH2:22][O:21][C:19](=[O:20])[CH3:18])[C@@H:24]([O:38][C:39](=[O:40])[CH3:41])[C@H:25]([O:34][C:35](=[O:36])[CH3:37])[C@H:26]3[O:30][C:31](=[O:32])[CH3:33])=[N:13][NH:14][C:15]=2[CH3:16])=[CH:8][CH:9]=1)[CH3:2]

参加物

5

反応物 2

HCID 101776alpha-D-Glucopyranosyl bromide, tetraacetateHCID 673356104-[(4-Ethylthiophenyl)methyl]-1,2-dihydro-5-methyl-3h-pyrazol-3-one

生成物 1

HCID 673347924-((4-ethylthiophenyl)methyl]-5-methyl-3-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyloxy)-1H-pyrazole収率 37.6%

試薬・触媒・溶媒 2

HCID 178418647HCID 178418647、化合物触媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a suspension of 4-[(4-ethylthiophenyl)methyl]-1,2-dihydro-5-methyl-3H-pyrazol-3-one (1.6 g) and acetobromo-α-D-glucose (2.9 g) in tetrahydrofuran (30 mL) was added silver carbonate (2.1 g), and the mixture was stirred under shading the light at 60° C. overnight. The reaction mixture was purified by column chromatography on aminopropyl silica gel (eluent: tetrahydrofuran) and further column chromatography on silica gel (eluent: hexane/ethyl acetate=1/3) to give 4-[(4-ethylthiophenyl)methyl]-5-methyl-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-1H-pyrazole (1.4 g).

後処理

  1. customat 60° C.
  2. customovernight
  3. customThe reaction mixture was purified by column chromatography on aminopropyl silica gel (eluent: tetrahydrofuran) and further column chromatography on silica gel (eluent: hexane/ethyl acetate=1/3)

出典と根拠

ORDレコード
ord-3ed1aca0a08245a8b5c6dfa4d562e9ee
出典データセット
uspto-grants-2006_08
特許番号
US07084123B2

関連ノート

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