化工社化工社 化学情報印刷レポート · 研究参考用
Sulfuric Acid → (2R,3S,4S,5S)-5-(acetoxymethyl)tetrahydrofuran-2,3,4-triyl triacetate
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Sulfuric Acid | HCID 1118 | — |
| 反応物 | Lithium Carbonate | HCID 11125 | — |
| 反応物 | L-Ribose | HCID 90428 | — |
| 反応物 | 1,2,3,5-tetra-O-acetyl-L-ribofuranose | HCID 11493434 | — |
| 溶媒 | Acetic Acid | HCID 176 | — |
| 溶媒 | Methanol | HCID 887 | — |
| 溶媒 | Water | HCID 962 | — |
| 溶媒 | Isopropanol | HCID 3776 | — |
| 溶媒 | Acetic Anhydride | HCID 7918 | — |
| 生成物 | (2R,3S,4S,5S)-5-(acetoxymethyl)tetrahydrofuran-2,3,4-triyl triacetate | HCID 908100 | 60% |
反応手順
In Non-Patent Document 6, L-ribose is used as a starting material, the methylation of the hydroxyl group at 1-position is carried out in methanol in the presence of sulfuric acid, the resultant mixture is then treated with lithium carbonate, the acetylation is then carried out in acetic acid and acetic anhydride, and concentrated sulfuric acid and acetic anhydride are further added thereto to carry out the acetolysis. A crude product is a mixture of α/β-anomers of 1,2,3,5-tetra-O-acetyl-L-ribofuranose. The crude product is treated with water and isopropyl alcohol to obtain 1,2,3,5-tetra-O-acetyl-β-L-ribofuranose at a total yield of 60%.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US08394935B2 |
| 出典データセット | uspto-grants-2013_03 |
| ORD ID | ord-9025124fd92c45129b3beb332837a7c3 |
| 出典メモ | uspto-grants-2013_03 |