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

HRID 619691Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 619691
[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'-cyanoethoxydiisopropylphos-phoramidite derivitized nucleoside is obtained by standard literature procedures, M. J. Gait, ed., Oligonucleotide Synthesis. A Practical Approach, (IRL Press, Washington, D.C., 1984) or through the procedure of Example 25A.

Aufarbeitung

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Quellen und Nachweise

ORD-Eintrag
ord-bd9d0cdd69934663ac887ad8626483ca
Quelldatensatz
uspto-grants-1999_09
Patentnummer
US05959096

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