HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Methanol → 2'-O-{2-[(Dimethylamino)oxy]ethyl}-5-methyluridine
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | Methanol | HCID 887 | — |
| Edukt | Triethylamine | HCID 8471 | — |
| Edukt | N,N-Diethylethanamine trihydrofluoride | HCID 175505 | — |
| Edukt | 5'-O-tert-butyldiphenylsilyl-2'-O-[N,N-dimethylaminooxyethyl)-5-methyluridine | HCID 22947701 | — |
| Lösungsmittel | Dichloromethane | HCID 6344 | — |
| Lösungsmittel | Tetrahydrofuran | HCID 8028 | — |
| Produkt | 2'-O-{2-[(Dimethylamino)oxy]ethyl}-5-methyluridine | HCID 22947699 | 92,5% |
Reaktionsschritte
Triethylamine trihydrofluoride (3.91 mL, 24.0 mmol) was dissolved in dry THF and triethylamine (1.67 mL, 12 mmol, dry, kept over KOH). This mixture of triethylamine-2HF was then added to 5′-O-tert-butyldiphenylsilyl-2′-O-[N,N-dimethylaminooxyethyl]-5-methyluridine (1.40 g, 2.4 mmol) and stirred at room temperature for 24 hrs. Reaction was monitored by TLC (5% MeOH in CH2Cl2). Solvent was removed under vacuum and the residue placed on a flash column and eluted with 10% MeOH in CH2Cl2 to get 2′-O-(dimethylaminooxyethyl)-5-methyluridine (766 mg, 92.5%).
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US07098192B2 |
| Quelldatensatz | uspto-grants-2006_08 |
| ORD ID | ord-0cafb7267e3a476788662141fc2d8f29 |
| Quellennotiz | uspto-grants-2006_08 |