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Volumn 44, Issue 45, 2003, Pages 8321-8323

A highly stereocontrolled and efficient synthesis of α- and β-pseudouridines

Author keywords

C nucleoside; Cycloetherification; Selective reduction

Indexed keywords

PSEUDOURIDINE;

EID: 0141888343     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.09.103     Document Type: Article
Times cited : (38)

References (22)
  • 1
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    • For a review, see Maden, B. E. H. Nature 1997, 389, 129.
    • (1997) Nature , vol.389 , pp. 129
    • Maden, B.E.H.1
  • 3
    • 0028575379 scopus 로고
    • Schweitzer, B. A.; Kool, E. T. J. Org. Chem. 1994, 59, 7238
    • See, for example: (a) Schweitzer, B. A.; Kool, E. T. J. Org. Chem. 1994, 59, 7238;
    • (1994) J. Org. Chem , vol.59 , pp. 7238
    • Schweitzer, B.A.1    Kool, E.T.2
  • 9
    • 0037756730 scopus 로고    scopus 로고
    • Yoshikawa, T.; Kimura, S.; Hatano, T.; Okamoto, K.; Hayatsu, H.; Arimoto-Kobayashi, S. Food Chem. Toxicol. 2002, 40, 1165; see also, Monobe, M.; Arimoto-Kobayashi, S.; Ando, K. Mutation Res. 2003, 538, 93.
    • (2003) Mutation Res. , vol.538 , pp. 93
    • Monobe, M.1    Arimoto-Kobayashi, S.2    Ando, K.3
  • 10
    • 0033548537 scopus 로고    scopus 로고
    • Grohen, P. J.; Chow, C. S. Tetrahedron Lett. 1999, 40, 2049
    • (a) Grohen, P. J.; Chow, C. S. Tetrahedron Lett. 1999, 40, 2049;
    • (1999) Tetrahedron Lett , vol.40 , pp. 2049
    • Grohen, P.J.1    Chow, C.S.2
  • 11
    • 37049108048 scopus 로고
    • and references cited therein. Brown, D. M.; Ogden, R. C. J. Chem. Soc., Perkin Trans. 1 1981, 723 and references cited therein.
    • (b) For earlier syntheses of α- and β-pseudouridines, see Brown, D. M.; Ogden, R. C. J. Chem. Soc., Perkin Trans. 1 1981, 723 and references cited therein.
    • (1981) J. Chem. Soc., Perkin Trans. 1 , vol.723
    • Brown, D.M.1    Ogden, R.C.2
  • 13
    • 0343035759 scopus 로고    scopus 로고
    • note
    • The original procedure without the inclusion of sodium sulfate gave 4 in 40% yield, accompanied by the protected δ-lactone and 2,3-O-isopropylidene-D-ribonolactone, see Csuk, R.; Kühn, M.; Ströhl, D. Tetrahedron 1997, 53, 1311. See Scheme 1 for the optimized and modified procedure.
  • 15
    • 0141904348 scopus 로고
    • Mitsunobu, O. Synthesis 1981, 1
    • for reviews, see: (b) Mitsunobu, O. Synthesis 1981, 1;
    • (1981) Synthesis , vol.1
    • Mitsunobu, O.1
  • 17
    • 85031064804 scopus 로고    scopus 로고
    • note
    • D +12.0° (c 8.5, MeOH).
  • 18
    • 85031055953 scopus 로고    scopus 로고
    • note
    • D -37.2° (c 0.5, MeOH).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.