HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Sulfuric Acid → (2R,3S,4S,5S)-5-(acetoxymethyl)tetrahydrofuran-2,3,4-triyl triacetate
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | Sulfuric Acid | HCID 1118 | — |
| Edukt | Lithium Carbonate | HCID 11125 | — |
| Edukt | L-Ribose | HCID 90428 | — |
| Edukt | 1,2,3,5-tetra-O-acetyl-L-ribofuranose | HCID 11493434 | — |
| Lösungsmittel | Acetic Acid | HCID 176 | — |
| Lösungsmittel | Methanol | HCID 887 | — |
| Lösungsmittel | Water | HCID 962 | — |
| Lösungsmittel | Isopropanol | HCID 3776 | — |
| Lösungsmittel | Acetic Anhydride | HCID 7918 | — |
| Produkt | (2R,3S,4S,5S)-5-(acetoxymethyl)tetrahydrofuran-2,3,4-triyl triacetate | HCID 908100 | 60% |
Reaktionsschritte
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%.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US08394935B2 |
| Quelldatensatz | uspto-grants-2013_03 |
| ORD ID | ord-9025124fd92c45129b3beb332837a7c3 |
| Quellennotiz | uspto-grants-2013_03 |