Thymidine, 3'-deoxy-3'-fluoro-, 5'-acetate → 3'-Fluorothymidine

HRID 1647545

Reaktionsgleichung

Reaktionsgleichung von HRID 1647545
C([O:4][CH2:5][C@H:6]1[O:10][C@@H:9]([N:11]2[CH:19]=[C:17]([CH3:18])[C:15](=[O:16])[NH:14][C:12]2=[O:13])[CH2:8][C@@H:7]1[F:20])(=O)C.C[O-].[Na+]>CO>[F:20][C@@H:7]1[C@@H:6]([CH2:5][OH:4])[O:10][C@@H:9]([N:11]2[CH:19]=[C:17]([CH3:18])[C:15](=[O:16])[NH:14][C:12]2=[O:13])[CH2:8]1

Komponenten

4

Edukt 2

HCID 453016Thymidine, 3'-deoxy-3'-fluoro-, 5'-acetateHCID 10942334Sodium Methoxide

Produkt 1

HCID 330393'-FluorothymidineAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a round-bottomed flask equipped with a magnetic spinbar and rubber septum was added 40 mg (0.1399 mmoles) 1-(5-O-acetyl-3-fluoro-2,3-dideoxy-β-D-erythro -pentofuranosyl)thymine, 9.1 mg (0.1679 mmoles) NaOMe powder and MeOH (1.4 mL). The mixture was allowed to stir for @2 hours at room temperature. The solvent was removed in vacuo and the resulting residue was purified by silica gel flash-chromatography to yield 1-(3-fluoro-2,3-dideoxy-β-D-erythro-pentofuranosyl)thymine (85%, 29 mg) as a white powder.

Aufarbeitung

  1. customTo a round-bottomed flask equipped with a magnetic spinbar and rubber septum
  2. customThe solvent was removed in vacuo
  3. customthe resulting residue was purified by silica gel flash-chromatography

Quellen und Nachweise

ORD-Eintrag
ord-0a599f193a39474b8baec751b1dc65d1
Quelldatensatz
uspto-grants-1995_07
Patentnummer
US05432273

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