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Volumn 3, Issue 7, 2001, Pages 1025-1028

2′-C-branched ribonucleosides. 2. Synthesis of 2′-C-β-trifluoromethyl pyrimidine ribonucleosides

Author keywords

[No Author keywords available]

Indexed keywords

PYRIMIDINE DERIVATIVE; RIBONUCLEOSIDE;

EID: 0035810365     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0155687     Document Type: Article
Times cited : (32)

References (39)
  • 14
    • 0032511950 scopus 로고    scopus 로고
    • and references therein
    • It has been reported that the reactions at C-1 of carbohydrates via cationic intermediates are much more difficult to achieve when a trifluoromethyl group is attached to C-2. Logothetis, T. A.; Eilitz, U.; Hiller, W.; Burger, K. Tetrahedron 1998, 54, 14023 and references therein.
    • (1998) Tetrahedron , vol.54 , pp. 14023
    • Logothetis, T.A.1    Eilitz, U.2    Hiller, W.3    Burger, K.4
  • 15
    • 0025649186 scopus 로고
    • Seebach argued on the basis of van der Waal hemispheres that a trifluoromethyl group is between two and three times larger than a methyl group. See: Seebach, D. Angew Chem., Int. Ed. Engl. 1990, 29, 1320. Other assessments suggest that the steric influence of the trifluoromethyl group is closer to that of an isopropyl group or even a tert-butyl group. See: (a) Smart, B. E.; Middleton, W. J. J. Am. Chem. Soc. 1987, 109, 4982.
    • (1990) Angew Chem., Int. Ed. Engl. , vol.29 , pp. 1320
    • Seebach, D.1
  • 16
    • 0042791385 scopus 로고
    • Seebach argued on the basis of van der Waal hemispheres that a trifluoromethyl group is between two and three times larger than a methyl group. See: Seebach, D. Angew Chem., Int. Ed. Engl. 1990, 29, 1320. Other assessments suggest that the steric influence of the trifluoromethyl group is closer to that of an isopropyl group or even a tert-butyl group. See: (a) Smart, B. E.; Middleton, W. J. J. Am. Chem. Soc. 1987, 109, 4982.
    • (1987) J. Am. Chem. Soc. , vol.109 , pp. 4982
    • Smart, B.E.1    Middleton, W.J.2
  • 21
    • 0042290371 scopus 로고    scopus 로고
    • note
    • 19F spectra are different from those of the corresponding 2′-C-β-trifluoromethyl-β-D-uridine 10 described in this paper.
  • 25
    • 0042290372 scopus 로고    scopus 로고
    • note
    • The anomers were separated with difficulty by silica gel chromatography as described in Supporting Information.
  • 36
    • 0020440848 scopus 로고
    • A few papers report the reaction of 3,5-di-O-acyl-D-1-ribofuranosyl chloride with reactive pyridine derivatives but not with nucleobases. See: (a) Konno, K.; Hayano, K.; Shirahama, H.; Saito, H.; Matsumoto, T. Tetrahedron 1982, 38, 3281.
    • (1982) Tetrahedron , vol.38 , pp. 3281
    • Konno, K.1    Hayano, K.2    Shirahama, H.3    Saito, H.4    Matsumoto, T.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.