Thiazolylketoses: A new class of versatile intermediates for glycoside synthesis

Chemical Communications

Volumn , Issue 21, 1999, Pages 2133-2145

  Dondoni, Alessandro ^a   Marra, Alberto ^a  

^a UNIVERSITY OF FERRARA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

AZIDE; GLYCOCONJUGATE; GLYCOSIDE; LACTONE DERIVATIVE; PHOSPHITE; SUGAR ALCOHOL; THIAZOLE DERIVATIVE;

ACETYLATION; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; REACTION ANALYSIS; REDUCTION; REVIEW; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0033533928     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a903758f     Document Type: Review

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30. Reviews: H. Kunz, Angew. Chem., Int. Ed. Engl., 1987, 26, 294; H. Paulsen, Angew. Chem., Int. Ed. Engl., 1990, 29, 823; H. Kunz, Pure Appl. Chem., 1993, 65, 1223; M. Meldal and K. Bock, Glycoconjugate J., 1994, 11, 59; G. Arsequell and G. Valencia, Tetrahedron: Asymmetry, 1997, 8, 2839.
31. Reviews: H. Kunz, Angew. Chem., Int. Ed. Engl., 1987, 26, 294; H. Paulsen, Angew. Chem., Int. Ed. Engl., 1990, 29, 823; H. Kunz, Pure Appl. Chem., 1993, 65, 1223; M. Meldal and K. Bock, Glycoconjugate J., 1994, 11, 59; G. Arsequell and G. Valencia, Tetrahedron: Asymmetry, 1997, 8, 2839.
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39. R. D. Guthrie, in The Carbohydrates, Chemistry and Biochemistry, ed. W. Pigman and D. Horton, Academic Press, San Diego, 1972, vol. 1A, pp. 423-478; M. Cerny and J. Stanek, Adv. Carbohydr. Chem. Biochem., 1977, 34, 23; H. Schiweck, M. Munir, K. M. Rapp, B. Schneider and M. Vogel, in Carbohydrates as Organic Raw Materials, ed. F. W. Lichtenthaler, VCH, Weinheim, 1991, pp. 57-94; M. Bols, Carbohydrate Building Blocks, Wiley, New York, 1996, pp. 43-48.
40. R. D. Guthrie, in The Carbohydrates, Chemistry and Biochemistry, ed. W. Pigman and D. Horton, Academic Press, San Diego, 1972, vol. 1A, pp. 423-478; M. Cerny and J. Stanek, Adv. Carbohydr. Chem. Biochem., 1977, 34, 23; H. Schiweck, M. Munir, K. M. Rapp, B. Schneider and M. Vogel, in Carbohydrates as Organic Raw Materials, ed. F. W. Lichtenthaler, VCH, Weinheim, 1991, pp. 57-94; M. Bols, Carbohydrate Building Blocks, Wiley, New York, 1996, pp. 43-48.
41. Selected recent papers: (a) A. Dondoni, H. M. Zuurmond and A. Boscarato, J. Org. Chem., 1997, 62, 8114;
42. (b) E. D. Rekaÿ, G. Rubinstenn, J.-M. Mallet and P. Sinaÿ, Synlett, 1998, 831;
43. (c) O. Jarreton, T. Skrydstrup, J.-F. Espinosa, J. Jiménez-Barbero and J.-M. Beau, Chem. Eur. J., 1999, 5, 430.
44. C-Trisaccharides: (a) T. Haneda, P. G. Goekjian, S. H. Kim and Y. Kishi, J. Org. Chem., 1992, 57, 490;
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46. (c) D. P. Sutherlin and R. W. Armstrong, J. Am. Chem. Soc., 1996, 118, 9802;
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53. G. Grynkiewicz and J. N. BeMiller, Carbohydr. Res., 1982, 108, 229; F. G. De las Heras, A. San Felix and P. Fernández-Resa, Tetrahedron, 1983, 39, 1617; D. B. Tulshian and B. Fraser-Reid, J. Org. Chem., 1984, 49, 518; R. W. Myers and Y. C. Lee, Carbohydr. Res., 1984, 132, 61; K. C. Nicolau, R. E. Dolle, A. Chucholowski and J. L. Randall, J. Chem. Soc., Chem. Commun., 1984, 1153; M. Hoffman and R. R. Schmidt, Liebigs Ann. Chem., 1985, 2403; Y. Araki, N. Kobayashi, K. Watanabe and Y. Ishido, J. Carbohydr. Chem., 1985, 4, 565; G. D. Kini, C. R. Petrie, W. J. Hennen, N. K. Dalley, B. E. Wilson and R. K. Robins, Carbohydr. Res., 1987, 159, 81; T. Mukaiyama and S. Kobayashi, Carbohydr. Res., 1987, 171, 81; M. T. García López, F. G. De las Heras and A. San Félix, J. Carbohydr. Chem., 1987, 6, 273; K. Tatsuta, J. Hayakawa and Y. Tatsuzawa, Bull. Chem. Soc. Jpn., 1989, 62, 490; K. N. Drew and P. H. Gross, J. Org. Chem., 1991, 56, 509.
54. G. Grynkiewicz and J. N. BeMiller, Carbohydr. Res., 1982, 108, 229; F. G. De las Heras, A. San Felix and P. Fernández-Resa, Tetrahedron, 1983, 39, 1617; D. B. Tulshian and B. Fraser-Reid, J. Org. Chem., 1984, 49, 518; R. W. Myers and Y. C. Lee, Carbohydr. Res., 1984, 132, 61; K. C. Nicolau, R. E. Dolle, A. Chucholowski and J. L. Randall, J. Chem. Soc., Chem. Commun., 1984, 1153; M. Hoffman and R. R. Schmidt, Liebigs Ann. Chem., 1985, 2403; Y. Araki, N. Kobayashi, K. Watanabe and Y. Ishido, J. Carbohydr. Chem., 1985, 4, 565; G. D. Kini, C. R. Petrie, W. J. Hennen, N. K. Dalley, B. E. Wilson and R. K. Robins, Carbohydr. Res., 1987, 159, 81; T. Mukaiyama and S. Kobayashi, Carbohydr. Res., 1987, 171, 81; M. T. García López, F. G. De las Heras and A. San Félix, J. Carbohydr. Chem., 1987, 6, 273; K. Tatsuta, J. Hayakawa and Y. Tatsuzawa, Bull. Chem. Soc. Jpn., 1989, 62, 490; K. N. Drew and P. H. Gross, J. Org. Chem., 1991, 56, 509.
55. G. Grynkiewicz and J. N. BeMiller, Carbohydr. Res., 1982, 108, 229; F. G. De las Heras, A. San Felix and P. Fernández-Resa, Tetrahedron, 1983, 39, 1617; D. B. Tulshian and B. Fraser-Reid, J. Org. Chem., 1984, 49, 518; R. W. Myers and Y. C. Lee, Carbohydr. Res., 1984, 132, 61; K. C. Nicolau, R. E. Dolle, A. Chucholowski and J. L. Randall, J. Chem. Soc., Chem. Commun., 1984, 1153; M. Hoffman and R. R. Schmidt, Liebigs Ann. Chem., 1985, 2403; Y. Araki, N. Kobayashi, K. Watanabe and Y. Ishido, J. Carbohydr. Chem., 1985, 4, 565; G. D. Kini, C. R. Petrie, W. J. Hennen, N. K. Dalley, B. E. Wilson and R. K. Robins, Carbohydr. Res., 1987, 159, 81; T. Mukaiyama and S. Kobayashi, Carbohydr. Res., 1987, 171, 81; M. T. García López, F. G. De las Heras and A. San Félix, J. Carbohydr. Chem., 1987, 6, 273; K. Tatsuta, J. Hayakawa and Y. Tatsuzawa, Bull. Chem. Soc. Jpn., 1989, 62, 490; K. N. Drew and P. H. Gross, J. Org. Chem., 1991, 56, 509.
56. G. Grynkiewicz and J. N. BeMiller, Carbohydr. Res., 1982, 108, 229; F. G. De las Heras, A. San Felix and P. Fernández-Resa, Tetrahedron, 1983, 39, 1617; D. B. Tulshian and B. Fraser-Reid, J. Org. Chem., 1984, 49, 518; R. W. Myers and Y. C. Lee, Carbohydr. Res., 1984, 132, 61; K. C. Nicolau, R. E. Dolle, A. Chucholowski and J. L. Randall, J. Chem. Soc., Chem. Commun., 1984, 1153; M. Hoffman and R. R. Schmidt, Liebigs Ann. Chem., 1985, 2403; Y. Araki, N. Kobayashi, K. Watanabe and Y. Ishido, J. Carbohydr. Chem., 1985, 4, 565; G. D. Kini, C. R. Petrie, W. J. Hennen, N. K. Dalley, B. E. Wilson and R. K. Robins, Carbohydr. Res., 1987, 159, 81; T. Mukaiyama and S. Kobayashi, Carbohydr. Res., 1987, 171, 81; M. T. García López, F. G. De las Heras and A. San Félix, J. Carbohydr. Chem., 1987, 6, 273; K. Tatsuta, J. Hayakawa and Y. Tatsuzawa, Bull. Chem. Soc. Jpn., 1989, 62, 490; K. N. Drew and P. H. Gross, J. Org. Chem., 1991, 56, 509.
57. G. Grynkiewicz and J. N. BeMiller, Carbohydr. Res., 1982, 108, 229; F. G. De las Heras, A. San Felix and P. Fernández-Resa, Tetrahedron, 1983, 39, 1617; D. B. Tulshian and B. Fraser-Reid, J. Org. Chem., 1984, 49, 518; R. W. Myers and Y. C. Lee, Carbohydr. Res., 1984, 132, 61; K. C. Nicolau, R. E. Dolle, A. Chucholowski and J. L. Randall, J. Chem. Soc., Chem. Commun., 1984, 1153; M. Hoffman and R. R. Schmidt, Liebigs Ann. Chem., 1985, 2403; Y. Araki, N. Kobayashi, K. Watanabe and Y. Ishido, J. Carbohydr. Chem., 1985, 4, 565; G. D. Kini, C. R. Petrie, W. J. Hennen, N. K. Dalley, B. E. Wilson and R. K. Robins, Carbohydr. Res., 1987, 159, 81; T. Mukaiyama and S. Kobayashi, Carbohydr. Res., 1987, 171, 81; M. T. García López, F. G. De las Heras and A. San Félix, J. Carbohydr. Chem., 1987, 6, 273; K. Tatsuta, J. Hayakawa and Y. Tatsuzawa, Bull. Chem. Soc. Jpn., 1989, 62, 490; K. N. Drew and P. H. Gross, J. Org. Chem., 1991, 56, 509.
58. G. Grynkiewicz and J. N. BeMiller, Carbohydr. Res., 1982, 108, 229; F. G. De las Heras, A. San Felix and P. Fernández-Resa, Tetrahedron, 1983, 39, 1617; D. B. Tulshian and B. Fraser-Reid, J. Org. Chem., 1984, 49, 518; R. W. Myers and Y. C. Lee, Carbohydr. Res., 1984, 132, 61; K. C. Nicolau, R. E. Dolle, A. Chucholowski and J. L. Randall, J. Chem. Soc., Chem. Commun., 1984, 1153; M. Hoffman and R. R. Schmidt, Liebigs Ann. Chem., 1985, 2403; Y. Araki, N. Kobayashi, K. Watanabe and Y. Ishido, J. Carbohydr. Chem., 1985, 4, 565; G. D. Kini, C. R. Petrie, W. J. Hennen, N. K. Dalley, B. E. Wilson and R. K. Robins, Carbohydr. Res., 1987, 159, 81; T. Mukaiyama and S. Kobayashi, Carbohydr. Res., 1987, 171, 81; M. T. García López, F. G. De las Heras and A. San Félix, J. Carbohydr. Chem., 1987, 6, 273; K. Tatsuta, J. Hayakawa and Y. Tatsuzawa, Bull. Chem. Soc. Jpn., 1989, 62, 490; K. N. Drew and P. H. Gross, J. Org. Chem., 1991, 56, 509.
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