Reaktionsgleichung
[C@@H:1]1([N:10]2[CH:18]=[N:17][C:16]3[C:11]2=[N:12][CH:13]=[N:14][C:15]=3[NH2:19])[O:7][C@H:6]([CH2:8][OH:9])[C@@H:4]([OH:5])[C@@H:2]1[OH:3].[C:20](Cl)(=[O:22])[CH3:21]>CN(C)C=O.N1C=CC=CC=1>[C:20]([O:9][CH2:8][C@H:6]1[O:7][C@@H:1]([N:10]2[CH:18]=[N:17][C:16]3[C:11]2=[N:12][CH:13]=[N:14][C:15]=3[NH2:19])[C@@H:2]([OH:3])[C@@H:4]1[OH:5])(=[O:22])[CH3:21]Komponenten
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To a stirred mixture of 2.67 g. of 9-(β-D-arabinofuranosyl)adenine and 100 ml. of 1:1 dimethylformamide-pyridine is added 0.79 g. of acetyl chloride at 25° C. The mixture is stirred, while being protected from moisture, for 1.5 hours, then treated with 50 g. of crushed ice and evaporated at reduced pressure. The residue is added to a 3× 40 cm. column of dry silica gel and the column is eluted sequentially with 500-ml. portions of 5, 10, 15 and 20% (v/v) methanol in chloroform. Two fractions of eluate (the 15 and 20% methanol in chloroform eluates) are combined and evaporated at reduced pressure to give the desired product 9-(5-O-acetyl-β-D-arabinofuranosyl)adenine; m.p. 197.5°-198.5° C. after crystallization from ethanol, [α]D23 = +23.6° (c = 1% in methanol), λmaxCH3OH = 258 nm (ε = 15,000), water solubility: 9.9 mg./ml.
Aufarbeitung
- additionTo a stirred mixture of 2.67 g
- customat 25° C
- customfor 1.5 hours
- additiontreated with 50 g
- customof crushed ice and evaporated at reduced pressure
- additionThe residue is added to a 3× 40 cm
- washcolumn of dry silica gel and the column is eluted sequentially with 500-ml
- customevaporated at reduced pressure
Quellen und Nachweise
- ORD-Eintrag
- ord-43e6af8678c348f18e9a30af771d5d43
- Quelldatensatz
- uspto-grants-1978_01
- Patentnummer
- US04069382
Verknüpfte Notizen
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