Purine → Nebularine

HRID 268513

Reaction equation

HRID 268513 reaction equation
[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

Participants

5

Reactant 3

HCID 1044Purine2×HCID 21705897Ammonia methanolHCID 131710119Chlorotriacetylribofuranose

Product 1

HCID 68368Nebularine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

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.

Sources & evidence

ORD record
ord-b9a10572cee545b7be20058119fe82e0
Source dataset
uspto-grants-1976_03
Patent number
US03947488

Linked notes

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