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Volumn , Issue 9 SPEC. ISS., 2003, Pages 1271-1274

An efficient route to pyrimidine nucleosides with the 2,3-anhydro-β-D-lyxofuranosyl stereochemistry

Author keywords

Anhydrosugars; Carbohydrates; Epoxides; Glycosylations; Nucleosides

Indexed keywords

2,3 ANHYDRO BETA DEXTRO LYXOFURANOSYL PYRIMIDINE NUCLEOSIDE; NUCLEOSIDE DERIVATIVE; PYRIMIDINE NUCLEOSIDE; SUGAR; UNCLASSIFIED DRUG;

EID: 0038780848     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-40335     Document Type: Article
Times cited : (13)

References (38)
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    • See, for example: (a) Huryn, D. M.; Okabe, M. Chem. Rev. 1992, 92, 1745. (b) Chen, Y. C. J.; Hansske, F.; Janda, K. D.; Robins, M. J. J. Org. Chem. 1991, 56, 3410. (c) Roussev, C. D.; Simeonov, M. F.; Petkov, D. D. J. Org. Chem. 1997, 62, 5238. (d) Miah, A.; Reese, C. B.; Song, Q.; Sturdy, Z.; Neidle, S.; Simpson, I. J.; Read, M.; Rayner, E. J. Chem. Soc., Perkin Trans. 1 1998, 3277. (e) Hirota, K.; Takasu, H.; Sajiki, H. Heterocycles 2000, 52, 1329.
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    • See, for example: (a) Huryn, D. M.; Okabe, M. Chem. Rev. 1992, 92, 1745. (b) Chen, Y. C. J.; Hansske, F.; Janda, K. D.; Robins, M. J. J. Org. Chem. 1991, 56, 3410. (c) Roussev, C. D.; Simeonov, M. F.; Petkov, D. D. J. Org. Chem. 1997, 62, 5238. (d) Miah, A.; Reese, C. B.; Song, Q.; Sturdy, Z.; Neidle, S.; Simpson, I. J.; Read, M.; Rayner, E. J. Chem. Soc., Perkin Trans. 1 1998, 3277. (e) Hirota, K.; Takasu, H.; Sajiki, H. Heterocycles 2000, 52, 1329.
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    • For representative examples: (a) Codington, J. F.; Fecher, R.; Fox, J. J. J. Org. Chem. 1962, 27, 163. (b) Williams, N. R. Adv. Carbohydr. Chem. Biochem. 1970, 25, 109. (c) Hollenberg, D. H.; Watanabe, K. A.; Fox, J. J. J. Med. Chem. 1977, 20, 113.
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    • 0008811610 scopus 로고
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    • 0026535656 scopus 로고
    • For additional examples see: (a) Chang, N. C.; Burchanel, R.; Fecher, R.; Duschinsky, R.; Fox, J. J. J. Am. Chem. Soc. 1961, 83, 4060. (b) Shiragami, H.; Tanaka, Y.; Uchide, Y.; Iwagami, H.; Izawa, K.; Yukawa, T. Nucleosides Nucleotides 1992, 11, 391. (c) Reichman, U.; Hollenberg, D. H.; Chu, C. K.; Watanabe, K. A.; Fox, J. J. J. Org. Chem. 1976, 41, 2042. (d) Robins, M. J.; Wilson, J. S.; Madej, D.; Low, N. H.; Hansske, F.; Wnuk, S. F. J. Org. Chem. 1995, 60, 7902.
    • (1992) Nucleosides Nucleotides , vol.11 , pp. 391
    • Shiragami, H.1    Tanaka, Y.2    Uchide, Y.3    Iwagami, H.4    Izawa, K.5    Yukawa, T.6
  • 13
    • 0017159087 scopus 로고
    • For additional examples see: (a) Chang, N. C.; Burchanel, R.; Fecher, R.; Duschinsky, R.; Fox, J. J. J. Am. Chem. Soc. 1961, 83, 4060. (b) Shiragami, H.; Tanaka, Y.; Uchide, Y.; Iwagami, H.; Izawa, K.; Yukawa, T. Nucleosides Nucleotides 1992, 11, 391. (c) Reichman, U.; Hollenberg, D. H.; Chu, C. K.; Watanabe, K. A.; Fox, J. J. J. Org. Chem. 1976, 41, 2042. (d) Robins, M. J.; Wilson, J. S.; Madej, D.; Low, N. H.; Hansske, F.; Wnuk, S. F. J. Org. Chem. 1995, 60, 7902.
    • (1976) J. Org. Chem. , vol.41 , pp. 2042
    • Reichman, U.1    Hollenberg, D.H.2    Chu, C.K.3    Watanabe, K.A.4    Fox, J.J.5
  • 14
    • 0028807212 scopus 로고
    • For additional examples see: (a) Chang, N. C.; Burchanel, R.; Fecher, R.; Duschinsky, R.; Fox, J. J. J. Am. Chem. Soc. 1961, 83, 4060. (b) Shiragami, H.; Tanaka, Y.; Uchide, Y.; Iwagami, H.; Izawa, K.; Yukawa, T. Nucleosides Nucleotides 1992, 11, 391. (c) Reichman, U.; Hollenberg, D. H.; Chu, C. K.; Watanabe, K. A.; Fox, J. J. J. Org. Chem. 1976, 41, 2042. (d) Robins, M. J.; Wilson, J. S.; Madej, D.; Low, N. H.; Hansske, F.; Wnuk, S. F. J. Org. Chem. 1995, 60, 7902.
    • (1995) J. Org. Chem. , vol.60 , pp. 7902
    • Robins, M.J.1    Wilson, J.S.2    Madej, D.3    Low, N.H.4    Hansske, F.5    Wnuk, S.F.6
  • 18
    • 0037572109 scopus 로고    scopus 로고
    • note
    • 2S: C, 54.74; H 4.98. Found: C, 54.70; H, 4.95.
  • 19
    • 0038247728 scopus 로고    scopus 로고
    • note
    • 3S: C, 51.60, 4.69. Found: C, 51.66; H, 4.73.
  • 20
    • 0037910195 scopus 로고    scopus 로고
    • note
    • 3 was added before the solution was allowed to warm to room temperature. The resulting solution was filtered through Celite, dried, filtered, and concentrated to yield a crude oil that was purified by chromatography.
  • 22
    • 0038247734 scopus 로고    scopus 로고
    • note
    • 6: 456.1172, found 456.1168.
  • 26
    • 0038247736 scopus 로고    scopus 로고
    • 20: Ref. 2c
    • (d) 20: Ref. 2c.
  • 35
    • 0036245577 scopus 로고    scopus 로고
    • See, for example: (a) Amann, N.; Wagenknecht, H.-A. Synlett 2002, 687. (b) Whale, R. F.; Coe, P. L.; Walker, R. T. Nucleosides Nucleotides 1991, 10, 1615. (c) Flynn, B. L.; Macolino, V.; Crisp, G. T. Nucleosides Nucleotides 1991, 10, 763. (d) Hobbs, F. W. Jr. J. Org. Chem. 1989, 54, 3420.
    • (2002) Synlett , pp. 687
    • Amann, N.1    Wagenknecht, H.-A.2
  • 36
    • 0025992749 scopus 로고
    • See, for example: (a) Amann, N.; Wagenknecht, H.-A. Synlett 2002, 687. (b) Whale, R. F.; Coe, P. L.; Walker, R. T. Nucleosides Nucleotides 1991, 10, 1615. (c) Flynn, B. L.; Macolino, V.; Crisp, G. T. Nucleosides Nucleotides 1991, 10, 763. (d) Hobbs, F. W. Jr. J. Org. Chem. 1989, 54, 3420.
    • (1991) Nucleosides Nucleotides , vol.10 , pp. 1615
    • Whale, R.F.1    Coe, P.L.2    Walker, R.T.3
  • 37
    • 0025822543 scopus 로고
    • See, for example: (a) Amann, N.; Wagenknecht, H.-A. Synlett 2002, 687. (b) Whale, R. F.; Coe, P. L.; Walker, R. T. Nucleosides Nucleotides 1991, 10, 1615. (c) Flynn, B. L.; Macolino, V.; Crisp, G. T. Nucleosides Nucleotides 1991, 10, 763. (d) Hobbs, F. W. Jr. J. Org. Chem. 1989, 54, 3420.
    • (1991) Nucleosides Nucleotides , vol.10 , pp. 763
    • Flynn, B.L.1    Macolino, V.2    Crisp, G.T.3
  • 38
    • 33845185176 scopus 로고
    • See, for example: (a) Amann, N.; Wagenknecht, H.-A. Synlett 2002, 687. (b) Whale, R. F.; Coe, P. L.; Walker, R. T. Nucleosides Nucleotides 1991, 10, 1615. (c) Flynn, B. L.; Macolino, V.; Crisp, G. T. Nucleosides Nucleotides 1991, 10, 763. (d) Hobbs, F. W. Jr. J. Org. Chem. 1989, 54, 3420.
    • (1989) J. Org. Chem. , vol.54 , pp. 3420
    • Hobbs F.W., Jr.1


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