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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
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | alpha-D-Glucopyranosyl bromide, tetraacetate | HCID 101776 | — |
| 反応物 | 4-(4-Isopropoxybenzyl)-5-methyl-1H-pyrazol-3(2H)-one | HCID 15542324 | — |
| 触媒 | HCID 178418647 | HCID 178418647 | — |
| 溶媒 | Tetrahydrofuran | HCID 8028 | — |
| 生成物 | 4-[(4-Isopropoxy-phenyl)methyl]-5-methyl-3-(2,3,4,6-tetra-o-acetyl-beta-d-glucopyranosyloxy)-1h-pyrazole | HCID 67335077 | 39% |
反応手順
To a suspension of 1,2-dihydro-4-[(4-isopropoxyphenyl)methyl]-5-methyl-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 under shading the light at 65° C. overnight. The reaction mixture was purified by column chromatography on aminopropyl silica gel (eluent: tetrahydrofuran). Further purification by preparative thin layer chromatography on silica gel (developing solvent: ethyl acetate/hexane=2/1) afforded 4-[(4-isopropoxyphenyl)methyl]-5-methyl-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-1H-pyrazole (42 mg).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US07084123B2 |
| 出典データセット | uspto-grants-2006_08 |
| ORD ID | ord-c5ed056b08414006a18d1d645c955333 |
| 出典メモ | uspto-grants-2006_08 |