Pyridine, hydrofluoride (1:1) → 2'Fluoro-2'-deoxyuridine

HRID 363237Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 363237
[CH:1]1[C:15](=[O:16])[N:14]=[C:13]2[N:3]([C@@H:4]3[O:8][C@H:7]([CH2:9][OH:10])[C@@H:6]([OH:11])[C@@H:5]3[O:12]2)[CH:2]=1.C1C=CN=CC=1.[FH:23]>O1CCOCC1>[F:23][C@@H:5]1[C@H:6]([OH:11])[C@@H:7]([CH2:9][OH:10])[O:8][C@H:4]1[N:3]1[CH:2]=[CH:1][C:15](=[O:16])[NH:14][C:13]1=[O:12]

Komponenten

4

Edukt 2

HCID 64774Pyridine, hydrofluoride (1:1)HCID 8061382,2'-Anhydrouridine

Produkt 1

HCID 1508512'Fluoro-2'-deoxyuridineAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

2,2'-Cyclouridine is treated with a solution of 70% hydrogen fluoride/pyridine in dioxane at 120° C. for ten hours to provide after solvent removal a 75% yield of 2'-deoxy-2'-fluorouridine. The 5'-DMT and 3'-cyanoethoxydiisopropylphosphoramidite derivitized nucleoside is obtained by standard literature procedures [Gait, Ed., Oligonucleotide Synthesis. A Practical Approach, IRL Press, Washington, D.C. (1984)], or according to the procedure of Example 1A.

Aufarbeitung

  1. customto provide

Quellen und Nachweise

ORD-Eintrag
ord-64a27b1333414f24a0f3989088582b32
Quelldatensatz
uspto-grants-1999_02
Patentnummer
US05872232

Notizen zur Reaktion

Wird geladen…