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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 23240Erstellt: 24. Oktober 2026

Methanol → 2'-O-{2-[(Dimethylamino)oxy]ethyl}-5-methyluridine

https://huagongshe.com/de/reaction/23240

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktMethanolHCID 887—
EduktTriethylamineHCID 8471—
EduktN,N-Diethylethanamine trihydrofluorideHCID 175505—
Edukt5'-O-tert-butyldiphenylsilyl-2'-O-[N,N-dimethylaminooxyethyl)-5-methyluridineHCID 22947701—
LösungsmittelDichloromethaneHCID 6344—
LösungsmittelTetrahydrofuranHCID 8028—
Produkt2'-O-{2-[(Dimethylamino)oxy]ethyl}-5-methyluridineHCID 2294769992,5%

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 removed under vacuum and the residue placed on a flash column and eluted with 10% MeOH in CH2Cl2 to get the title compound (766 mg, 92.5%). Rf 0.27 (5% MeOH in CH2Cl2). MS (FAB⊕) m/e 346 (M+H⊕)

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS06849723B2
Quelldatensatzuspto-grants-2005_02
ORD IDord-b1bfb384d1f04335bed777c650be455b
Quellennotizuspto-grants-2005_02