HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Trityl chloride → 9-(2',3',5'-O-triacetyl-b-D-ribofuranosyl)-2,6-dichloropurine
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | Trityl chloride | HCID 6456 | — |
| Edukt | Pentyl nitrite | HCID 10026 | — |
| Edukt | Potassium Carbonate | HCID 11430 | — |
| Edukt | 2-amino-6-chloro-9-(2,3,5-O-triacetyl-beta-D-ribofuranosyl)-9H-purine | HCID 86743189 | — |
| Lösungsmittel | Dichloromethane | HCID 6344 | — |
| Produkt | 9-(2',3',5'-O-triacetyl-b-D-ribofuranosyl)-2,6-dichloropurine | HCID 131717899 | 74,3% |
Reaktionsschritte
n-Pentyl nitrite (98 g, 838 mM) is added over one hour at room temperature under nitrogen to a mixture of the compound of Example 2 (350 g, 819 mM), triphenylmethyl chloride (500 g, 1.79 M) and potassium carbonate (65 g) in CH2Cl2 (3 L). The resulting mixture is heated at reflux for 20 minutes, cooled to room temperature and filtered. The filtrate is concentrated in vacuo, and the resulting residue is purified by column chromatography on silica gel (2.5 kg, ethyl acetate/hexane 1:4-3:7) to yield the title compound as a pale yellow solid (272 g, 74%).
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US05208327 |
| Quelldatensatz | uspto-grants-1993_05 |
| ORD ID | ord-7f1279cc1061468d873edb8b1a1305bf |
| Quellennotiz | uspto-grants-1993_05 |