Ammonia methanol → 2'-deoxy-4'-thiocytidine

HRID 716136Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 716136
N.CO.C([O:12][C@@H:13]1[C@@H:17]([CH2:18][O:19]C(=O)C2C=CC=CC=2)[S:16][C@@H:15]([N:28]2[CH:35]=[CH:34][C:32]([NH2:33])=[N:31][C:29]2=[O:30])[CH2:14]1)(=O)C1C=CC=CC=1>CO>[C@@H:15]1([N:28]2[CH:35]=[CH:34][C:32]([NH2:33])=[N:31][C:29]2=[O:30])[S:16][C@H:17]([CH2:18][OH:19])[C@@H:13]([OH:12])[CH2:14]1

Komponenten

4

Edukt 2

HCID 21705897Ammonia methanolHCID 89975628HCID 89975628, Verbindung

Produkt 1

HCID 100374252'-deoxy-4'-thiocytidineAusbeute 90,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

1 mL of a 7 mol/L ammonia/methanol solution was added to a solution of 9.6 mg of 1-(2-deoxy-3,5-bis-O-benzoyl-4-thio-β-D-ribofuranosyl)cytosine in 1 mL of methanol, and the obtained mixture was then stirred at room temperature for 3 hours. Thereafter, the solvent was distilled away under reduced pressure, and the obtained residue was then purified by silica gel column chromatography (ethyl acetate/methanol=95/5 to 30/70), so as to obtain 4.7 mg of 1-(2-deoxy-4-thio-β-D-ribofuranosyl)cytosine in the form of a white solid.

Aufarbeitung

  1. distillationThereafter, the solvent was distilled away under reduced pressure
  2. customthe obtained residue was then purified by silica gel column chromatography (ethyl acetate/methanol=95/5 to 30/70)

Quellen und Nachweise

ORD-Eintrag
ord-307ce66456a84e8e85398b9373443b18
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09187514B2

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