Synthesis of 2′,3′-Didehydro-2′,3′-dideoxynucleosides by Reaction of 5′-O-Protected Nucleoside 2′,3′-Dimesylates with Lithium Areneselenolates

Journal of Organic Chemistry

Volumn 62, Issue 11, 1997, Pages 3751-3753

  Clive, Derrick L J ^a   Sgarbi, Paulo W M ^a   Wickens, Philip L ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

2',3' DIDEOXYNUCLEOSIDE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030989214     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo962079p     Document Type: Article

References (31)

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3. Simple vicinal dimesylates have been converted into olefins by the action of an iodide ion, but this method does not appear to be useful in the nucleoside series, at least, as judged by a test case we examined (see ref 2).
4. (a) Reich, H. J.; Chow, F.; Shah, S. K. J. Am. Chem. Soc. 1979, 101, 6638.
5. (b) Clive, D. L. J.; Russell, C. G.; Suri, S. C. J. Org. Chem. 1982, 47, 1632.
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8. 3B plays any role in the reaction. cf. Dittmer, D. C.; Zhang, Y.; Discordia, R. P. J. Org. Chem. 1994, 59, 1004.
9. Gladysz, J. A.; Hornby, J. L.; Garbe, J. E. J. Org. Chem. 1978, 43, 1204.
10. A significant byproduct was the result of displacement of both OMs groups by PhSe (see Experimental Section).
11. For examples of vicinal bis(phenyl selenides) that collapse spontaneously to olefins, see: Piettre, S.; Janousek, Z.; Merenyi, R.; Viehe, H. G. Tetrahedron 1985, 41, 2527. In the case of 1,2-bis-(methylseleno) compounds, chromatography over silica gel causes decomposition to dimethyl diselenide and the corresponding olefin: Hermans, B.; Colard, N.; Hevesi, L. Tetrahedron Lett. 1992, 33, 4629. cf. Gulliver, D. J.; Hope, E. G.; Levason, W.; Murray, S. G.; Potter, D. M.; Marshall, G. L. J. Chem. Soc., Perkin Trans. 2 1984, 429.
12. For examples of vicinal bis(phenyl selenides) that collapse spontaneously to olefins, see: Piettre, S.; Janousek, Z.; Merenyi, R.; Viehe, H. G. Tetrahedron 1985, 41, 2527. In the case of 1,2-bis-(methylseleno) compounds, chromatography over silica gel causes decomposition to dimethyl diselenide and the corresponding olefin: Hermans, B.; Colard, N.; Hevesi, L. Tetrahedron Lett. 1992, 33, 4629. cf. Gulliver, D. J.; Hope, E. G.; Levason, W.; Murray, S. G.; Potter, D. M.; Marshall, G. L. J. Chem. Soc., Perkin Trans. 2 1984, 429.
13. For examples of vicinal bis(phenyl selenides) that collapse spontaneously to olefins, see: Piettre, S.; Janousek, Z.; Merenyi, R.; Viehe, H. G. Tetrahedron 1985, 41, 2527. In the case of 1,2-bis-(methylseleno) compounds, chromatography over silica gel causes decomposition to dimethyl diselenide and the corresponding olefin: Hermans, B.; Colard, N.; Hevesi, L. Tetrahedron Lett. 1992, 33, 4629. cf. Gulliver, D. J.; Hope, E. G.; Levason, W.; Murray, S. G.; Potter, D. M.; Marshall, G. L. J. Chem. Soc., Perkin Trans. 2 1984, 429.
14. Batchelor, R. J.; Einstein, F. W. B.; Gay, I. D.; Gu, J.-H.; Johnston, B. D.; Pinto, B. M. J. Am. Chem. Soc. 1989, 111, 6582.
15. Murata, S.; Suzuki, T.; Yanagisawa, A.; Suga, S. J. Heterocycl. Chem. 1991, 28, 433.
16. 3-BHLi (cf. ref 6).
17. 4 in EtOH.
18. Morgan, G. T.; Kellett, R. E. J. Chem. Soc. 1926, 1080.
19. 4 in EtOH.
20. Morgan, G. T.; Drew, H. D. K. J. Chem. Soc. 1925, 2307.
21. A THF solution of the selenol acid (Kamiyama, T.; Enomoto, S.; Inoue, M. Chem. Pharm. Bull. 1985, 33, 5184) was added to a suspension of NaH (2.1 mole of per mol selenol acid). The suspension was stirred for 5 min and was then transferred by cannula into a solution of 13a (1 mol) in THF. No change was detected (TLC) after 24 h.
22. 3-BHLi).
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26. Prepared (88% yield) by the reported method (Kuszmann, J.; Sohár, P. Carbohydr. Res. 1979, 74, 187). The parent diol was prepared (36% yield) according to: Chittenden, G. J. F. Carbohydr. Res. 1982, 108, 81.
27. Prepared (88% yield) by the reported method (Kuszmann, J.; Sohár, P. Carbohydr. Res. 1979, 74, 187). The parent diol was prepared (36% yield) according to: Chittenden, G. J. F. Carbohydr. Res. 1982, 108, 81.
28. (a) Kuszmann, J.; Sohár, P. Carbohydr. Res. 1980, 83, 63.
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30. Lambert, J. B.; Fabricius, D. M.; Hoard, J. A. J. Org. Chem. 1979, 44, 1480. In preparing the butenylnaphthalene, we used allyllithium, generated (Seyferth, D.; Weiner, M. A. J. Org. Chem. 1961, 26, 4797) from triphenyl(2-propenyl)stannane.
31. Lambert, J. B.; Fabricius, D. M.; Hoard, J. A. J. Org. Chem. 1979, 44, 1480. In preparing the butenylnaphthalene, we used allyllithium, generated (Seyferth, D.; Weiner, M. A. J. Org. Chem. 1961, 26, 4797) from triphenyl(2-propenyl)stannane.