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Volumn 37, Issue 12, 1996, Pages 1995-1998

Novel nucleosides via intramolecular functionalization of 2,2′-anhydrouridine derivatives

Author keywords

[No Author keywords available]

Indexed keywords

NUCLEOSIDE DERIVATIVE; URIDINE DERIVATIVE;

EID: 0029892303     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00227-4     Document Type: Article
Times cited : (24)

References (32)
  • 1
    • 0000335222 scopus 로고
    • For recent reviews of nucleoside chemistry and modified nucleosides in oligonucleotide synthesis, see: (a) Huryn, D. M.; Okabe, M. Chem. Rev. 1992, 92, 1745-1768.
    • (1992) Chem. Rev. , vol.92 , pp. 1745-1768
    • Huryn, D.M.1    Okabe, M.2
  • 12
    • 0043058567 scopus 로고    scopus 로고
    • reference 3
    • (c) reference 3
  • 15
    • 0002062166 scopus 로고
    • R.T. Walker; De Clercq, E.; Eckstein, F., Eds.; Plenum Press: New York, and references therein
    • (b) Moffatt, J.G. in Nucleoside Analogues; R.T. Walker; De Clercq, E.; Eckstein, F., Eds.; Plenum Press: New York, 1979; 71-164 and references therein.
    • (1979) Nucleoside Analogues , pp. 71-164
    • Moffatt, J.G.1
  • 22
    • 0043058554 scopus 로고
    • (b) Intramolecular ring opening of a 2,2′-anhydrouridine by a phosphate has been reported, see: Ogilvie, K. K.; Iwacha, D. Can. J. Chem. 1970, 48, 862-864.
    • (1970) Can. J. Chem. , vol.48 , pp. 862-864
    • Ogilvie, K.K.1    Iwacha, D.2
  • 23
    • 0042557581 scopus 로고    scopus 로고
    • note
    • 2,2′-Anhydrouridine is prepared from uridine and diphenyl carbonate (DMF/ HMPA; 110°C) on a kilogram scale according to the published procedure.6
  • 24
    • 0041555556 scopus 로고    scopus 로고
    • note
    • 13C NMR spectra, and C, H, N analysis or mass spectra.
  • 25
    • 0000762868 scopus 로고
    • For an example of intramolecular cyclofunctionalization of an epoxy alcohol-derived trichloroacetimidate, see: Bernet, B.; Vasella, A. Tetrahedron Lett. 1983, 24, 5491-5494.
    • (1983) Tetrahedron Lett. , vol.24 , pp. 5491-5494
    • Bernet, B.1    Vasella, A.2
  • 27
    • 0042056693 scopus 로고    scopus 로고
    • note
    • During the DBU catalyzed cyclization of OTBDMS derivative 12, a minor amount (9% isolated yield) of a cyclization product resulting from nucleophilic attack by the carbamate carbonyl oxygen was formed, as was a significant amount of N-O desilylated product (36%).
  • 32
    • 0041555549 scopus 로고    scopus 로고
    • note
    • 5-Iodouridine is unstable under these reaction conditions.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.