A one-pot synthesis of D-ribonucleosides using natural phosphate doped with KI in HMDS

Letters in Organic Chemistry

Volumn 3, Issue 4, 2006, Pages 313-314

  Lazrek, Hassan Bihi ^a   Ouzebla, Driss ^a   Rochdi, Abdellali ^a   Redwane, Nezha ^a   Vasseur, Jean Jacques ^b  

^a FACULTÉ DES SCIENCES SEMLALIA   (Morocco)

^b UNIVERSITÉ DE MONTPELLIER   (France)

Author keywords

Natural phosphate; Nucleosides; Potassium iodide

Indexed keywords

EID: 33746137345     PISSN: 15701786     EISSN: None     Source Type: Journal    
DOI: 10.2174/157017806776114531     Document Type: Article

References (12)

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7. 31.
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9. a) Alahiane, A.; Rochdi, A.; Taourirte, M.; Redwane, N.; Sebti, S.; Engels, J.W.; Lazrek, H. B. Nucleosides Nucleotides Nucleic Acids 2003, 22, 109-114;
10. (b) Rochdi, A.; Taourirte, M.; Redwane, N.; Sebti, S.; Engels, J.W.; Lazrek, H. B. Nucleosides Nucleotides Nucleic Acids 2003, 22, 679-681.
11. Typical procedure for the catalyst preparation: To a solution of potassium iodide (1 g) in water (5 mL) was added natural phosphate (3 g), and the mixture was stirred for 15 min. The mixture was then evaporated to dryness.
12. Typical procedure for one -pot synthesis: To uracil (112 mg, 1 mmol) was added hexamethyldisilazane (4 mL) and ammonium sulphate (10 mg). The mixture was refluxed for two hours. To the obtained clear solution was added 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose (453 mg, 0.9 mmol), the catalyst (473 mg, 0.8 mmol of KI) and acetonitrile (5 mL). After being refluxed overnight, the mixture was filtered and the solvent evaporated. The crude product was purified by column chromatography. The desired product was obtained with 55% yield (Table 1, entry 4).