Synthesis of 6-alkyl and 6-aryl substituted 9-β-D-ribofuranosyl purines via the nickel catalyzed coupling of grignard reagents to 2′,3′,5′-tris-0-(t-butyldimethylsilysl)-9-β-D-ribofuranosyl-6-chloropurine
✍ Scribed by Donald E. Bergstrom; P.Anantha Reddy
- Publisher
- Elsevier Science
- Year
- 1982
- Tongue
- French
- Weight
- 257 KB
- Volume
- 23
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
A series of 6-substituted purine nucleosides have been synthesized in mcderate yield by the nickel catalyzed cross coupling reaction between alkyl-and aryl-Griqnard reagents and 2',3',5'-tris-@-(t-butyldimethylsilyl)-9-~-~-ribofuranosy1-6-chloropurine. Adenosine analogues with alkyl and aryl group linked to the amino group at C-6 show a considerable range of biological activity.' For example, N6-cyclohexyladenosine strongly binds Al-adenosine receptors2 and ~~6-(4-hydroxy-3-methyl-trans-butenyl)adenosine(zeatin riboside) is an active cytokinin. 3 The amino group at C-6 is not always necessary for activity. The most potent inhibitors of nucleoside transport in erythrocytes are purine nucleosides to which a substituted benzyl group is attached via sulfur to C-6. 4 A number of 6-alkylated purines5 and their nucleoside analogues6 show interesting biological activity. However, despite efforts to synthesize 6-alkyl and 6-aryl nucleoside analcgues for biological testing no direct broadly useful synthetic route to this class of compounds has been developed.