化工社化工社 化学情報印刷レポート · 研究参考用
Imidazole → (2R,3S,5R)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]tetrahydrofuran-2,3,4-triol
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Imidazole | HCID 795 | — |
| 反応物 | D-Arabinose | HCID 66308 | — |
| 反応物 | tert-Butyldiphenylchlorosilane | HCID 94078 | — |
| 溶媒 | Dimethylformamide | HCID 6228 | — |
| 溶媒 | Ethyl Acetate | HCID 8857 | — |
| 生成物 | (2R,3S,5R)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]tetrahydrofuran-2,3,4-triol | HCID 131737102 | 25.7% |
反応手順
To a stirred solution of D-arabinose (50 g, 0.33 mol) in DMF (500 mL) was added imidazole (45 g, 0.66 mol) and tert-butylchlorodiphenylsilane (109 g, 0.4 mol). After being stirred at room temperature for 2 hours, the resulting solution was diluted with EtOAc (2000 mL), washed with water, brine and dried over Na2SO4. The organic layer was concentrated in vacuo and the residue was purified by column chromatography on silica gel (eluting with 1:11 EtOAc in petroleum ether) to afford 33 g of (2R,3S,5R)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]tetrahydrofuran-2,3,4-triol (compound 25a).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US09441008B2 |
| 出典データセット | uspto-grants-2016_09 |
| ORD ID | ord-8f78f4534f214d0aa8ff1322a63c61e7 |
| 出典メモ | uspto-grants-2016_09 |