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Volumn 53, Issue 37, 2014, Pages 9893-9897

Synthesis and duplex-stabilizing properties of fluorinated N-methanocarbathymidine analogues locked in the C3'-endo conformation

Author keywords

asymmetric synthesis; diastereoselectivity; duplex thermal stability; fluorination; modified nucleosides

Indexed keywords

FLUORINATION; SCAFFOLDS; THERMODYNAMIC STABILITY; ISOMERS;

EID: 84906946276     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201405283     Document Type: Article
Times cited : (28)

References (55)
  • 6
    • 79952066733 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2011, 50, 2284-2288
    • (2011) Angew. Chem. Int. Ed. , vol.50 , pp. 2284-2288
  • 32
    • 84869391995 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2012, 51, 11863-11866.
    • (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 11863-11866
  • 33
    • 28344456399 scopus 로고    scopus 로고
    • Compound 4 was prepared by the Morita-Baylis-Hillman reaction of cyclopentenone and formaldehyde in 97 % yield.
    • Compound 4 was prepared by the Morita-Baylis-Hillman reaction of cyclopentenone and formaldehyde in 97 % yield., H. Ito, Y. Takenaka, S. Fukunishi, K. Iguchi, Synthesis 2005, 3035-3038.
    • (2005) Synthesis , pp. 3035-3038
    • Ito, H.1    Takenaka, Y.2    Fukunishi, S.3    Iguchi, K.4
  • 38
    • 0032541271 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 1998, 37, 1986-2012.
    • (1998) Angew. Chem. Int. Ed. , vol.37 , pp. 1986-2012
  • 42
    • 0001728270 scopus 로고
    • The oxidation of 7 by other methods (e.g. Swern, PCC, IBX) gave 8 in lower yield. We also attempted to prepare the alcohol of 8 (i.e. without the TBS protecting group) from 4 directly by using the enantioselective Charette modification of the Simmons-Smith reaction with an optically active dioxaborolane, but did not observe any product., A. B. Charette, H. Juteau, J. Am. Chem. Soc. 1994, 116, 2651-2652.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 2651-2652
    • Charette, A.B.1    Juteau, H.2
  • 43
    • 33746494993 scopus 로고
    • The oxidative method to prepare this enone by using a selenoxide elimination did not proceed well in this case.
    • Y. Ito, T. Hirao, T. Saegusa, J. Org. Chem. 1978, 43, 1011-1013. The oxidative method to prepare this enone by using a selenoxide elimination did not proceed well in this case.
    • (1978) J. Org. Chem. , vol.43 , pp. 1011-1013
    • Ito, Y.1    Hirao, T.2    Saegusa, T.3
  • 48
    • 84862646886 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2012, 51, 6176-6180.
    • (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 6176-6180


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.