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Volumn 11, Issue 2, 2000, Pages 629-638

Higher iodinated analogues of D-glucose: Syntheses of 3-C-iodomethyl, 6-C-iodomethyl and 6-C-iodophenyl derivatives

Author keywords

[No Author keywords available]

Indexed keywords

CARBOHYDRATE DERIVATIVE; GLUCOSE DERIVATIVE; IODINE;

EID: 0034635622     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00518-2     Document Type: Article
Times cited : (5)

References (40)
  • 1
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    • Synthèse de sucres iodés; vers l'imagerie SPECT du transport du D-glucose
    • Comet, M.; Vidal, M., Eds. Presse Universitaire de Grenoble: France,
    • For a review, see: Morin, C. Synthèse de sucres iodés; vers l'imagerie SPECT du transport du D-glucose. In Radiopharmaceutiques, Chimie des traceurs et applications biologiques. Comet, M.; Vidal, M., Eds. Presse Universitaire de Grenoble: France, 1998; pp. 295-305.
    • (1998) In Radiopharmaceutiques, Chimie des Traceurs et Applications Biologiques , pp. 295-305
    • Morin, C.1
  • 3
    • 0034338105 scopus 로고    scopus 로고
    • in press, and references cited therein.
    • Hamant, S.; Mathieu, J.-P.; Morin, C.; Trimcev, I.; Vidal, M. Bioorg. Med. Chem. Lett. 1994, 4, 1687-1690; see also: Morin, C.; Ogier, L. J. Carbohydr. Chem. 2000, 19, in press, and references cited therein.
    • (2000) J. Carbohydr. Chem. , vol.19
    • Morin, C.1    Ogier, L.2
  • 6
    • 0027908696 scopus 로고
    • For 3-(3-iodoprop-2-en)-yl-D-glucose, see: Goodman, M. M.; Kabalka, G. W.; Waterhouse, R. N.; Daniel, G. B. J. Labelled Compds Radiopharm. 1991, 30, 278-279. For 3-(2-iodoethyl)-D-glucose, see: Bignan, G. Morin, C.; Vidal, M. Carbohydr. Res. 1993, 248, 371-375.
    • (1993) Carbohydr. Res. , vol.248 , pp. 371-375
    • Bignan, G.1    Morin, C.2    Vidal, M.3
  • 7
    • 0342771126 scopus 로고    scopus 로고
    • For 3-deoxy-3-iodo-D-glucose, see: Tsuya, A.; Shigematsu, A. Ger. Off. 2817336; see also: Kloster, G.; Laufer, P.; Wutz, W.; Stöcklin, G. J. Labelled Compds Radiopharm. 1982, 19, 1626-1628.
    • Ger. Off. 2817336
    • Tsuya, A.1    Shigematsu, A.2
  • 19
    • 0032573614 scopus 로고    scopus 로고
    • Grenoble
    • After completion of this work (Ogier, L. Thèse de Doctorat, Grenoble, 1998), an efficient preparation of epoxide 7 has been disclosed: Soler, T.; Bachki, A.; Falvello, L. R.; Foubelo, F.; Yus, M. Tetrahedron: Asymmetry 1998, 9, 3939-3943.
    • (1998) Thèse de Doctorat
    • Ogier, L.1
  • 22
    • 0000206070 scopus 로고
    • For advantages of betaiodoethers in radiolabelling see Ref. 2.
    • The adverse beta effect of oxygen in such displacements has been discussed; see: Fleet, G. W. J. Chem. Brit. 1989, 25, 287-292. For advantages of betaiodoethers in radiolabelling see Ref. 2.
    • (1989) J. Chem. Brit. , vol.25 , pp. 287-292
    • Fleet, G.W.1
  • 29
    • 0343196663 scopus 로고    scopus 로고
    • Blériot, Y.; Veighey, C. R.; Smelt, K. H.; Cadefau, J.; Stalmans, W.; Biggadike, K.; Lane, A. L.; Müller, M.; Watkin, D. J.; Fleet, G. W. J. Tetrahedron: Asymmetry 1996, 9, 2761-2772. Masaguer, C. F.; Blériot, Y.; Charlwood, J.; Winchester, B. G.; Fleet, G. W. J. Tetrahedron 1997, 53, 15147-15156.
    • (1997) Tetrahedron , vol.53 , pp. 15147-15156
    • Masaguer, C.F.1    Blériot, Y.2    Charlwood, J.3    Winchester, B.G.4    Fleet, G.W.J.5
  • 38
    • 0033529647 scopus 로고    scopus 로고
    • For a recent approach to C-phenyl terminally substituted carbohydrates, see: Bruns, R.; Wernicke, A.; Köll, P. Tetrahedron 1999, 55, 9793-9800.
    • (1999) Tetrahedron , vol.55 , pp. 9793-9800
    • Bruns, R.1    Wernicke, A.2    Köll, P.3
  • 39
    • 0342336160 scopus 로고    scopus 로고
    • Although the absolute configurations at C-6 of C-iodomethyl and C-iodophenyl derivatives are the same, priority rules using Cahn-Ingold-Prelog descriptors result in 6S and 6R naming, respectively.
    • Although the absolute configurations at C-6 of C-iodomethyl and C-iodophenyl derivatives are the same, priority rules using Cahn-Ingold-Prelog descriptors result in 6S and 6R naming, respectively.
  • 40
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    • The use of stannylated precursors may allow radiolabelling with high specific activity; for a review of tin intermediates to get radiopharmaceuticals, see: Ali, H.; Van Lier, J. E. Synthesis 1996, 423-445.
    • (1996) Synthesis , pp. 423-445
    • Ali, H.1    Van Lier, J.E.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.