- Studies in Nucleosides: Part XVI - Synthesis of Azathioprine Analogues
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6--9-(1'-tetrahydrofuranyl)purine (4) , 6--9-(1'-tetrahydropyranyl)purine (5), 9-hydroxyethoxymethyl-6-purine (6), 6--9-(β-D-ribofuranosyl)purine (12), 9-(α-D-arabinofuranosyl)-6-purine (16) and 9-(β-D-2'-deoxyribofuranosyl)-6-purine (11) have been synthesised.Condensation of 1 with dihydrofuran and dihydropyran gives 4 and 5 respectively in excellent yields.The reaction of 1 separately with benzoyloxyethoxymethylene chloride (2), 1-O-acetylribose derivative (7) and 1-chloro-2-deoxyribose derivative (9) and of the chloromercuric complex (13) with 1-bromoarabinose derivative (14) gives the blocked nucleosides (3, 8, 10 and 15) respectively.Deblocking of the nucleosides with methanolic ammonia finally affords 6, 12, 11 and 16 respectively.
- Mishra, Anil,Pratap, Ram,Bhakuni, D. S.
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p. 847 - 850
(2007/10/02)
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