A procedure for facile synthesis of nucleosides using N, O-Bistrimethyl- silylacetamide in the presence of natural phosphate coated with potassium iodide

Letters in Organic Chemistry

Volumn 7, Issue 3, 2010, Pages 196-199

  Baddi, Laila ^a   Smietana, Michael ^c   Sebti, Saïd ^b   Vasseur, Jean Jacques ^c   Lazrek, Hassan B ^a  

^a FACULTÉ DES SCIENCES SEMLALIA   (Morocco)

^b FACULTÉ DES SCIENCES BEN M SIK   (Morocco)

^c UNIVERSITÉ DE MONTPELLIER   (France)

Author keywords

Catalyst; D L nucleosides; N Glycosylation; Natural phosphate

Indexed keywords

EID: 77951445926     PISSN: 15701786     EISSN: None     Source Type: Journal    
DOI: 10.2174/157017810791112441     Document Type: Article

References (20)

1. Raney, A. K.; Hamatake, R.K.; Hong, Z. Agents in clinical development for the treatment of chronic hepatitis B. Expert Opin. Investig. Drugs, 2003, 12, 1281.
2. Mathe, C.; Gosselin, G. L-nucleoside enantiomers as antivirals drugs. Mini Rev. Antiviral Res., 2006, 71, 276.
3. Vorbruggen, H.; Ruh-Pohlenz, C. Synthesis of nucleosides: Org. React., 2000, 55, 1.
4. Vorbruggen, H.; Hofle, G. On the Mechanism of nucleoside synthesis. Chem. Ber., 1981, 114, 1256.
5. (a)Vorbruggen, H.; Krolikiewicz, K.; Bennua, B. Nucleoside synthesis with trimethylsilyl triflate and perchlorate as catalyst. Chem. Ber., 1981, 114, 1234
6. (b) Vorbruggen, H.; Bennua, B. A new simplified nucleoside synthesis. Chem. Ber., 1981, 114, 1279.
7. (a) Sebti, S.; Zahouilly, M.; Lazrek, H.B.; Mayoral, J.A.; Macquerrie, D.J. Phosphates: new generation of liquid-phase heterogeneous catalysts in organic chemistry. Curr. Org. Chem., 2008, 12, 203.
8. 7 synthesis of a-amino phosphonates under solvent-free conditions at room temperature. Lett. Org. Chem., 2005, 2, 428.
9. (c) Zahouily, M.; Mezdar, A.; Elmakssoudi, A.; Mounir, B.; Rayadh, A.; Sebti, S.; Lazrek, H. B Comparison of different Lewis acids supported on natural phosphate as new catalysts for chemoselective dithioacetalization of carbonyl compounds under solvent-free conditions. ARKIVOC, 2006, 31.
10. (d) Alahiane, A.; Rochdi, A.; Taourirte,M.; Redwane, N.; Sebti, S.; Engels, J. W.; Lazrek, H. B. Building blocks for polyamide nucleic acids: facile synthesis using potassium fluoride doped natural phosphate as basic catalyst. Nucleosides Nucleotides Nucleic Acids, 2003, 22, 109.
11. 2], as shown by X-ray diffraction and chemical analysis. The surface area of NP was measured at μm2 g- 1 (nitrogen adsorption) and the total pore volume was 0.005 cm3 g-1.
12. Lazrek, H.B.; Rochdi, A.; Redwane, N.; D. Ouzebla, D.; Vasseur J.J. A one-pot synthesis of D-ribonucleosides using natural phosphate doped with KI in HMDS. Lett. Org. Chem., 2006, 3, 313.
13. (a) Lazrek, H.B.; Ouzebla, D.; Baddi, L; Vasseur, J.J. Glycosylation reaction via a mild and efficient one-pot reaction using doped natural phosphate with iodine as catalyst. Nucleosides Nucleotides Nucleic Acids, 2007, 26, 1095.
14. (b) Lazrek, H.B.; Baddi, L.; Smietena, M.; Sebti, S.; Zahouily, M.; Vasseur, J.J. One- pot synthesis of antiviral acyclovir and other nucleosides derivatives using doped natural phosphate as lewis acid catalyst. Nucleosides Nucleotides Nucleic Acids, 2008, 27, 1107.
15. Gosselin, G.; Bergogne, M-C.; Imbach, J. L. Synthesis and antiviral evaluation of β-L-Xylo-fuanosyl nucleosides of the five naturally occurring nucleic acid bases. J. Heterocycl. Chem., 1993, 30, 1229
16. (b) Wang, Z.; Prudhomme, d.R.; Buck, J.R.; Park, M.; Rizzo, C.J. Stereocontrolled syntheses of deoxyribonucleosides via photoinduced electron-transfer deoxygenation of benzoyl-protected ribo- and arabinonucleosides. J. Org. Chem., 2000, 65, 5969.
17. Jooko, Y.; Shin, S.B.; Shim, J.H. Facile synthesis of 2-O- iodoacetyl protected glycosyl iodides: useful precursors of 1→2-linked 1,2-trans-glycosides. Org. Lett., 2009, 11, 609.
18. (a) Park, J.; Kawatkar, S.; Kim, J-H.; Boons, G-J. Stereoselective glycosylations of 2-azido-2-deoxy-glucosides using intermediate sulfonium ions. Org. Lett.,2007, 9, 1959
19. (b) Van well, R.M.; Ravindranathan Kartha, K.P.; Field, R. A. Iodine promoted glycosylation with glycosyl iodides: α-glycoside synthesis J. Carbohydr. Chem., 2005, 24, 463
20. (c) Lam, S-N.; Gervay-hague, Solution-phase hexasaccharide synthesis using glucosyl iodides. J. Org. Lett., 2002, 4, 2039.