N-Nitration, 15N-Labeling, and N-to-N Linking of Hydroxyl-Silylated Pyrimidine Nucleosides

Journal of Organic Chemistry

Volumn 62, Issue 5, 1997, Pages 1547-1549

  Ariza, Xavier ^a   Farràs, Jaume ^a   Serra, Carme ^a   Vilarrasa, Jaume ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

NITROGEN 15;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; ISOTOPE LABELING; METHODOLOGY; REACTION ANALYSIS;

EID: 0030995221     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9615514     Document Type: Article

References (24)

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2. 15N]-labeled AZT, see: Ariza, X.; Bou, V.; Vilarrasa, J.; Tereshko, V.; Campos, J. L. Angew. Chem., Int. Ed. Engl. 1994, 33, 2454.
3. (c) Bou, V. Nuevas reacciones en el campo de los nucleósidos. Ph.D. Thesis, Universitat de Barcelona, 1992.
4. For reviews, see: (a) Ueda, T. Chemistry of Nucleosides and Nucleotides; Townsend, L. B., Ed.; Plenum Press: New York, 1988. (b) Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis; Wiley: New York, 1991. (c) Kocienski, P. J. Protecting Groups; Thieme: Stuttgart, 1994. (d) van Look, G.; Simchen, G.; Heberle, J. Silylating Agents; Fluka Chemie AG: Buchs, 1995.
5. For reviews, see: (a) Ueda, T. Chemistry of Nucleosides and Nucleotides; Townsend, L. B., Ed.; Plenum Press: New York, 1988. (b) Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis; Wiley: New York, 1991. (c) Kocienski, P. J. Protecting Groups; Thieme: Stuttgart, 1994. (d) van Look, G.; Simchen, G.; Heberle, J. Silylating Agents; Fluka Chemie AG: Buchs, 1995.
6. For reviews, see: (a) Ueda, T. Chemistry of Nucleosides and Nucleotides; Townsend, L. B., Ed.; Plenum Press: New York, 1988. (b) Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis; Wiley: New York, 1991. (c) Kocienski, P. J. Protecting Groups; Thieme: Stuttgart, 1994. (d) van Look, G.; Simchen, G.; Heberle, J. Silylating Agents; Fluka Chemie AG: Buchs, 1995.
7. For reviews, see: (a) Ueda, T. Chemistry of Nucleosides and Nucleotides; Townsend, L. B., Ed.; Plenum Press: New York, 1988. (b) Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis; Wiley: New York, 1991. (c) Kocienski, P. J. Protecting Groups; Thieme: Stuttgart, 1994. (d) van Look, G.; Simchen, G.; Heberle, J. Silylating Agents; Fluka Chemie AG: Buchs, 1995.
8. Romea, P.; Aragonès, M.; Garcia, J.; Vilarrasa, J. J. Org. Chem. 1991, 56, 7038.
9. With smaller excesses (n = 2-4), uridine 2a afforded mainly the 2′-O-nitro compound, while thymidine 4a gave rise to mixtures of O-nitro and N,O-dinitro compounds (with n = 2, 80% of 3′-O-nitro derivative plus 10% of N,O-dinitro 4b; with n = 4, 30% of O-nitro plus 62% of 4b).
10. 5′ -dinitro derivative.
11. (a) The TIPDS group is known to be sensitive to aqueous basic media: Markiewicz, W. T. J. Chem. Res., Synop, 1979, 24.
12. (b) There are also examples of the moderate stability of TBDMS protecting groups under certain basic conditions: Reddy, M. P.; Farooqui, F.; Hanna, N. B. Tetrahedron Lett. 1995, 36, 8929 and references 1-3 therein.
13. (c) Also see: Fallois, L. L. H.; Décout, J.-L.; Fontecave, M. Tetrahedron Lett. 1995, 36, 9479.
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