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Original Articles

Synthesis of 1′,2′-Seco-nucleoside Analogues of AZT

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Pages 739-748 | Received 12 Sep 1991, Accepted 20 Nov 1991, Published online: 23 Sep 2006

References

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  • Lee , K.-H. , Wang , E.-C. , Hwang , L.-C. , Han , C.-H. and Tzeng , C.-C. March 1987 . The 4th Symposium on Heterocyclic Chemistry , March , Taiwan : Hsinchu . (b) Lee, K.-H.; Chen, Y.-L.; Huang, B.-R.; Tzeng, C.-C.; Zhu, Q.-Y.; Chou, T.-C. Nucleotides Nucleotides, 199110, 1407.
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  • In the text and Experimental Section, the butanetriols (4–8) are named and numbered in accordance with butanetriol nomenclature. The naming and numbering of the 1′,2′-seco-nucleosides follow nucleoside nomenclature in the text and schemes, however, in the Experimental Section butanetriol nomenclature is used.
  • Abushanab , E. , Vemishetti , P. , Leiby , R. W. , Singh , H. K. , Mikkilineni , A. B. , Wu , D. C.-J. , Saibaba , R. and Panzica , R. P. 1988 . J. Org. Chem. , 53 : 2598
  • Mitsunobu , O. 1981 . Synthesis , 1 (b) Cichy, A.F.; Saibaba, R.; El Subbagh, H.I.; Panzica, R.P.; Abushanab, E. J. Org. Chem., 199156, 4653.
  • Abushanab , E. , Bessodes , M. and Antonakis , K. 1984 . Tetrahedron Lett. , 25 : 3841
  • Panzica , R. P. , Abushanab , E. , Vemishetti , P. , Singh , H. K. and Leiby , R. W. August 1987 . 194th National Meeting of the American Chemical Society , August , Louisiana : New Orleans . MEDI 10
  • Dissolving this mixture in hexanes and allowing it to stand for 30 min at 4 °C precipitates most of the dihydro-DIAD (H2DIAD). After filtration and removal of solvent, the epoxide 7 is sufficiently pure for further use.
  • Vemishetti , P. , Abushanab , E. , Leiby , R. W. and Panzica , R. P. 1988 . J. Heterocycl. Chem. , 25 : 651

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