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alpha-D-Glucopyranosyl bromide, tetraacetate → 4-((4-ethylthiophenyl)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-Ethylthiophenyl)methyl]-1,2-dihydro-5-methyl-3h-pyrazol-3-one | HCID 67335610 | — |
| 触媒 | HCID 178418647 | HCID 178418647 | — |
| 溶媒 | Tetrahydrofuran | HCID 8028 | — |
| 生成物 | 4-((4-ethylthiophenyl)methyl]-5-methyl-3-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyloxy)-1H-pyrazole | HCID 67334792 | 37.6% |
反応手順
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).
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-3ed1aca0a08245a8b5c6dfa4d562e9ee |
| 出典メモ | uspto-grants-2006_08 |