Purine → Nebularine

HRID 268513

Reaktionsgleichung

Reaktionsgleichung von HRID 268513
[N:1]1[CH:9]=[C:8]2[C:4]([N:5]=[CH:6][NH:7]2)=[N:3][CH:2]=1.Cl[C@:11]1(CO)[O:16][C:14]([C:17](=[O:19])C)(O)[C@:13](C(=O)C)([OH:20])[C@:12]1(C(=O)C)[OH:24].CO.N>C(Cl)(Cl)Cl>[CH:9]1[C:8]2[N:7]=[CH:6][N:5]([C@@H:11]3[O:16][C@H:14]([CH2:17][OH:19])[C@@H:13]([OH:20])[C@H:12]3[OH:24])[C:4]=2[N:3]=[CH:2][N:1]=1

Komponenten

5

Edukt 3

HCID 1044Purine2×HCID 21705897Ammonia methanolHCID 131710119Chlorotriacetylribofuranose

Produkt 1

HCID 68368Nebularine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

Nebularine was prepared by the use of the thallous salt of purine in the procedure of Brown et al., J. Biol. Chem. 204, 1019 (1953), in place of the chloromercuri salt used therein. The thallous salt of purine is condensed with chlorotriacetylribofuranose and the resulting acetyl derivative hydrolyzed to the product with methanol-ammonia. Other experimental conditions were identical. Crystalline nebularine was obtained after chromatography of the crude product on silica-gel with chloroform.

Quellen und Nachweise

ORD-Eintrag
ord-b9a10572cee545b7be20058119fe82e0
Quelldatensatz
uspto-grants-1976_03
Patentnummer
US03947488

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