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1996 | 43 | 1 |

Tytuł artykułu

Some recent trends and progress in nucleoside synthesis

Autorzy

Warianty tytułu

Języki publikacji

EN

Abstrakty

EN
Some recent progress concerning the optimal combinations of Lewis acids and solvents for the synthesis of pyrimidine as well as purine nucleosides is reviewed. Furthermore, the novel condensation of persilyiated free sugars and heterocyclic bases in the presence of trimethylsilyl triflate to the corresponding persilyiated nucleosides is discussed.

Wydawca

-

Rocznik

Tom

43

Numer

1

Opis fizyczny

p.25-36

Twórcy

  • Research Laboratories, Schering AG, 13342 Berlin, Germany

Bibliografia

  • 1. Fuller, W.D., Sanchez, R. A. & Orgel, L..D. (1972) Studies in prebiotic synthesis. VII. Solid state synthesis of purine nucleosides.. /. Mol. Evo­lution 1, 249.
  • 2. Fuller, W.D., Sanchez, R.A. & Orgel, LD. (1972) Studies in prebiotic synthesis. VI. Synthesis of purine nucleosides. /. Mol. Biol. 67,6725.
  • 3. Vorbrüggen, H., Kjolikiewicz, K. & Bennua, B. (1981) Nucleoside syntheses. XXII. Nucleoside synthesis with trimethylsilyi triflate and Perchlorate as catalysis. Chem. Ber. 114,1234.
  • 4. Ototani, N. & Whistler. R.L. (1974) Preparation and antitumor activity of 4'-thioanalogs of 2',2'- -anhydro-1-ß-D-arabinofuranosylcytosine. /. Med. Chem. 17, 535.
  • 5. Secrist, J.A., Parker, W.B., Tiwari, K.N., I.ea Messini,S.C.,Shaddix,S.C,Rose, L.M., Bennett, L.L. & Montgomery, J.A. (1995) The synthesis and biological activity of certain 4'-thionu- cleosides. Nucleosides & Nucleotides 14,675.
  • 6. Langer, S.H., Connell, S.C. & Wender, I. (1958) Preparation and properties of trimethylsilyi ethers and related compounds. ). Org. Chem. 23, 50.
  • 7. Klebe, I.F. (1970) Silyl-proton exchange reac­tions. Acc. Chan. Res. 3,299.
  • 8. Zou, R. & Robins, M.J. (1987) High-yield regioselective synthesis of 9-glycosyl guanine nucleosides and analogues via coupling with 2-N-acetyl-6-0-diphenylcarbamoylguanine. Can. J. Chem. 65. 1436.
  • 9. Robins. M.J., Zou, R., Hansske, F., Madej, D. & Tyrell, D.I..J. (1989) Synthesis, transformation chemistry and biological activity of guanine nucleosides and analogues. Nucleosides & Nucleotides 8. 725.
  • 10. Garner, P. & Ramakanth,_S. (1988) A regio- controlled synthesis of N'- and N9-guanine nucleosides. /. Org. Chem. 53.1294.
  • 11. Vorbrüggen, H. & Höfle, G. (1981) Nucleoside syntheses XXIII. On the mechanism of nucleoside synthesis. Chem. Ber. 114,1256.
  • 12. Mahmood, K. Vasella, A. & Bernet, B. (1991) Deoxynitrosugars. XVII. Synthesis of ketose- derived nucleosides from 1-deoxy-l-nitro- ribose. Helv. Chim. Acta 74,1555.
  • 13. Mukaiyama, T., Matsutani, T. & Shimomura, N. (1994) Tin(II) chloride catalysed synthesis of ß-D-ribofuranosides. Chem. Lett. 2089.
  • 14. Mayr, H„ Gorath, G. & Bauer, B. (1994) Liquid sulfur dioxide as a Lcwis-acidic solvent for the alkylalion and alkoxyallylation of allylsilanes. Angew. Chemie Int. Ed. 33.788.
  • 15. von Altermatt, R. & Tamm. Ch. (1985) Synthese eines Tridecanucleosiddodecaphosphats, das die unnatürliche Base 2(llI)-Pyrimidinon enthält. Helv. Chim. Acta 88,475.
  • 16. Vorbrüggen, H., Królikiewicz, K. & Niedballa, U. (1975) Eine Neue Einfache Synthese von Cytidinen. Nucleosidsynthesen. XIV. Amine- rung von Heterocyclen. I. LiebigsAnn. Chem. 988
  • 17. Vorbrüggen, H. & Bennua, B. (1981) Nucleoside syntheses. XXV. A new simplified nucleoside synthesis. Chem. Ber. 114,1279.
  • 18. West, R., Wilson, L.S. & Powell, D.L (1979) Basicity of siloxanes, alkoxysilanes and ethers toward hydrogen bonding. /. Organomet. Chem. 178. 5-9.
  • 19. Shambayati, S., Blake, J.F., Wierschke, S.G.. Jorgensen, W.I.. & Schreiber, S.L. (1990) Struc­ture and basicity of silyl ethers: A crystallo- graphic and ab initio inquiry into the nature of silicon-oxygen interactions. /. Am. Chem. Soc. 112,697.
  • 20. Niedballa, U. & Vorbriiggen, H. (1974) A general synthesis of N-glycosides. 1. Synthesis of pvrimidine nucleosides. J. Org. Chem. 39,3654.
  • 21. Tsunoda. T., Suzuki, M. & Noyori. R. (1980) A facile procedure for acetalization under aprotic conditions. Tetrahedron Lett. 21.1357.
  • 22. Bennua-Skalmowski, B., Królikiewicz, K. & Vorbriiggen, H. (1995) A new simple nucleoside synthesis. Tetrahedron Lett. 36,7845.

Typ dokumentu

Bibliografia

Identyfikatory

Identyfikator YADDA

bwmeta1.element.agro-article-9de33593-e3e2-43f1-aff7-c39364d59334
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