Glycoside Synthesis from 1-Sulfur/Selenium-Substituted Derivatives: Xanthates, Thioimidates and Other Thio Derivatives

Handbook of Chemical Glycosylation: Advances in Stereoselectivity and Therapeutic Relevance

Volumn , Issue , 2008, Pages 329-361

  Szeja, Wiesław ^a   Grynkiewicz, Grzegorz ^b  

^a SILESIAN UNIVERSITY OF TECHNOLOGY   (Poland)

^b INDUSTRIAL CHEMISTRY RESEARCH INSTITUTE   (Poland)

Author keywords

Selenoglycosides; Sulfimides; Sulfones; Thio derivatives; Thioimidates; Xanthates

Indexed keywords

EID: 84891004692     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783527621644.ch4c     Document Type: Chapter

References (122)

1. Duus, F. (1979) Thiocarbonyl compounds, in Comprehensive Organic Chemistry vol. 3, (eds D. Barton and W.D. Ollis),Pergamon, pp. 373-487.
2. Crich, D. and Quintero, L. (1989) Chemical Reviews, 89, 1413-1432.
3. Walter, W. and Voss, J. (1970) The chemistry of thioamides inThe Chemistry of Amides (ed. J. Zabicky), Wiley Interscience, London, pp. 383-475.
4. Griffin, T.S.,Woods, T.S. and Klayman, D.J. (1975) Advances in Heterocyclic Chemistry, 18, 99-158.
5. Witczak, Z.J. (1986) Advances in Carbohydrate Chemistry and Biochemistry, 44, 91-145.
6. Manuel, J., Fernandez, G. and Mellet, C.O. (2000) Advances in Carbohydrate Chemistry and Biochemistry, 55, 35-135.
7. Horton, D. (1963) Methods in Carbohydrate Chemistry, 2, 433-437.
8. Marra, A. and Sinay, P. (1989) Carbohydrate Research, 187, 35-42.
9. Marra, A. and Sinay, P. (1990) Carbohydrate Research, 195, 303-308.
10. Marra, A., Gauffeny, F. and Sinay, P. (1991) Tetrahedron, 47, 5149-5160.
11. Trapper, F.D., Anderson, F.O. and Roy, R. (1992) Journal of Carbohydrate Chemistry, 11, 741-750.
12. Wandzik, I. and Szeja, W. (1998) Polish Journal of Chemistry, 72, 703-709.
13. Bogusiak, J., Wandzik, I. and Szeja, W. (1996) Carbohydrate Letters, 1, 411-416.
14. Guerard, D., Tatibouet, A., Gareau, Y. and Rollin, P. (1999) Organic Letters, 1, 521-522.
15. Pougny, J.-R. (1986) Journal of Carbohydrate Chemistry, 5, 529-535.
16. Nifantev, N.E., Tsvetkov, Y.E., Shashkov, A.S., Kononov, L.O., Menshov, V.M., Tuzikov, A.B. and Bovin, N. (1996) Journal of Carbohydrate Chemistry, 15, 939-953.
17. Greilich, U., Brescello, R., Jung, K.H. and Schmidt, R.R. (1996) Liebigs Annalen der Chemie, 663-672.
18. Bilberg, W. and Lonn, H. (1991) Tetrahedron Letters, 32, 7453-7456.
19. Bilberg, W. and Lonn, H. (1991) Tetrahedron Letters, 32, 7457-7458.
20. Lonn, H. and Stenvall, K. (1992) Tetrahedron Letters, 33, 115-116.
21. Martichonok, V. and Whitesides, G.M. (1996) The Journal of Organic Chemistry, 61, 1702-1706.
22. Boons, G.-J. and Demchenko, A.V. (2000) Chemical Reviews, 100, 4539-4565, and references therein.
23. Halkes, K.M., Hilaire, P.H.S., Jansson, A. H., Gotfreidsen, C.H. and Meldal, M. (2000) Journal of the Chemical Society Perkin Transactions, 2127-2133.
24. Sabesan, S., Neira, S., Davidson, F., Duus, J.O. and Bock, K. (1994) Journal of the American Chemical Society, 116, 1616-1634.
25. Ray, A.K., Nilsson, U. and Magnusson, G. (1992) Journal of the American Chemical Society, 114, 2256-2257.
26. Elofsson, M. and Kihlberg, J. (1995) Tetrahedron Letters, 36, 7499-7502.
27. Ercegovic, T. and Magnusson, G. (1995) The Journal of Organic Chemistry, 60, 3378-3384.
28. Wilstermann, M., Kononov, L.O., Nilsson, U., Ray, A.K. and Magnusson, G. (1995) Journal of the American Chemical Society, 117, 4742-4754.
29. Elofsson, M., Salvador, L.A. and Kihlberg, J. (1997) Tetrahedron, 53, 369-390.
30. Liebe, B. and Kunz, H. (1997) Angewandte Chemie (International Edition in English), 36, 618-621.
31. van Seeventer, P.B., Kerekgyarto, J., van Dorst, J.A.L.M., Halkes, K.M., Kamerling, J.P. and Vliegenthart, J.F.G. (1997) Carbohydrate Research, 300, 127-138.
32. Wilstermann, M. and Magnusson, G. (1997) The Journal of Organic Chemistry, 62, 7961-7971.
33. Ellervick, U. and Magnusson, G. (1998) The Journal of Organic Chemistry, 63, 9314-9322.
34. Ellervick, U., Grundberg, H. and Magnusson, G. (1998) The Journal of Organic Chemistry, 63, 9323-9338.
35. Salvatore, B.A. and Prestegard, J.H. (1998) Tetrahedron Letters, 39, 9319-9322.
36. Tietze, L.F., Janssen, C.O. and Gewert, J. A. (1998) European Journal of Organic Chemistry, 1887-1894.
37. Tietze, L.F. and Gretzke, D. (1998) European Journal of Organic Chemistry, 1895-1899.
38. Liebe, B. and Kunz, H. (1994) Tetrahedron Letters, 35, 8777-8778.
39. Pornsuriyasak, P., Kamat, M.N. and Demchenko, A.V. (2007) ACS Series, 960, 165-189.
40. ElAshry, H.S.H., Awad, L.F. and Atta, A.I. (2006) Tetrahedron, 62, 2943-2998.
41. Tejima, S. and Ishiguro, S. (1967) Chemical & Pharmaceutical Bulletin, 15, 255-263.
42. Lee, B.-H., Bertram, B., Schmezer, P., Frank, N. and Wiessler, M. (1994) Journal of Medicinal Chemistry, 123, 3154-3162.
43. Lee, B.-H., Bertram, B., Schmezer, P., Frank, N. and Wiessler, M. (1993) Royal Society of Chemistry, 123, 53-57.
44. Zinner, H. and Pfeifer, M. (1963) Chemische Berichte, 96, 432-437.
45. Zinner, H. and Peseke, K. (1965) Chemische Berichte, 98, 3515-3519.
46. Demchenko, A.V., Kamat, M.N. and De Meo, C. (2003) Synlett, 1287-1290.
47. Demchenko, A.V., Malysheva, N.N. and and De Meo, C. (2003) Organic Letters, 5, 455-458.
48. Demchenko, A.V., Pornsuriyasak, P., De Meo, C. and Malysheva, N.N. (2004) Angewandte Chemie (International Edition), 43, 3069-3072.
49. Mukaiyama, T., Nakatsuka, T. and Shoda, S.I. (1979) Chemistry Letters, 487-490.
50. Bogusiak, J. and Szeja, W. (1988) Chemistry Letters, 1975-1976.
51. Mereyala, H.B., Kulkarni, V.R., Ravi, D., Sharma, G.V.M., Rao, B.V. and Reddy, G. B. (1992) Tetrahedron, 48, 545-562.
52. Stewart, A.O. and Williams, R.M. (1985) Journal of the American Chemical Society, 107, 4289-4296.
53. Abdel-Rahman, A.A.H., El Ashry, E.S.H. and Schmidt, R.R. (2002) Carbohydrate Research 337, 195-206.
54. Khodair, A.I., Al-Masoudi, N.A. and Gesson, J.P. (2003) Nucleosides Nucleotides & Nucleic Acids, 22, 2061-2076.
55. Euzen, R., Ferrieres, V. and Plusquellec, D. (2005) The Journal of Organic Chemistry, 70, 847-855.
56. Bogusiak, J. (2005) Letters in Organic Chemistry, 2, 271-273.
57. Fourrey, J.-L. and Jouin, P. (1979) The Journal of Organic Chemistry, 44, 1892-1894.
58. Ernst B., Hart G.W. and Sinay P. (eds) (2000) Carbohydrates in Chemistry and Biology, vol. 1, Wiley-VCH Verlag GmbH, Weinheim, Germany. Chapters 2-9.
59. Jung, K.-H. and Schmidt, R.R. (2000) Chemical Reviews, 100, 4423-4442.
60. Davis, B.G. (2000) Journal of the Chemical Society, Perkin Transactions, 1, 2137-2160.
61. Boons, G.-J. (1996) Tetrahedron, 52, 1095-1121.
62. Schmidt, R.R. and Kinzy, W. (1994) Advances in Carbohydrate Chemistry and Biochemistry, 50, 21-123.
63. Danishefsky, S.J. and Bilodeau, M.T. (1996) Angewandte Chemie (International Edition in English), 35, 1380-1419.
64. Toshima, K. and Tatsuta, K. (1993) Chemical Reviews, 93, 1503-1531.
65. Douglas, N.L., Ley, S.V., Lucking, U. and Warriner, S.L. (1998) Journal of the Chemical Society Perkin Transactions, 1, 51-65.
66. Zhang, Z., Ollmann, I.R., Ye, X.-S., Wischnat, R., Baasov, T. and Wong, C.-H. (1999) Journal of the American Chemical Society, 121, 734-753.
67. Zhu, T. and Boons, G.-J. (2001) Organic Letters, 3, 4201-4203.
68. Mootoo, D.R., Konradsson, P., Udodong, U. and Fraser-Reid, B. (1988) Journal of the American Chemical Society, 110, 5583-5584.
69. Fraser-Reid, B., Wu, Z., Udodong, U.E. and Ottosson, H. (1990) The Journal of Organic Chemistry, 55, 6068-6070.
70. Baeschlin, D.K., Green, L.G.,Hahn, M.G., Hinzen, B., Ince, S.J. and Ley, S.V. (2000) Tetrahedron: Asymmetry, 11, 173-197.
71. Veeneman, G.H. and van Boom, J.H. (1990) Tetrahedron Letters, 31, 275-278.
72. Friesen, R.W. and Danishefsky, S.J. (1989) Journal of the American Chemical Society, 111, 6656-6660.
73. Nguyen, H.M., Poole, J.L. and Gin, D.Y. (2001) Angewandte Chemie (International Edition), 40, 414-417.
74. Yamago, S., Yamada, T., Hara, O., Ito, H., Mino, Y. and Yoshida, J.-I. (2001) Organic Letters, 3, 3867-3870.
75. Burkhart, F., Zhang, Z., Wacowich-Sgarbi, S. and Wong, C.-H. (2001) Angewandte Chemie (International Edition), 40, 1274-1277.
76. Mong, K.-K.T. and Wong, C.-H. (2002) Angewandte Chemie (International Edition), 41, 4087-4090.
77. Mong, K.-K.T., Lee, H.-K., Duron, S.G. and Wong, C.-H. (2003) Proceedings of the National Academy of Sciences of the United States of America, 100, 797-802.
78. Fugedi, P., Garegg, P.J., Oscarson, S., Rosen, G. and Silvanis, B.A. (1991) Carbohydrate Research, 211, 157-162.
79. Pornsuriyasak, P. and Demchenko, A.V. (2005) Tetrahedron: Asymmetry, 16, 433-439.
80. Bongat, A.F.G., Kamat, M.N. and Demchenko, A.V. (2007) The Journal of Organic Chemistry, 72, 1480-1483.
81. Jung, K.-H.,Muller,M. and Schmidt, R.R. (2000) Chemical Reviews, 100, 4423-4442.
82. Weingart, R. and Schmidt, R.R. (2000) Tetrahedron Letters, 41, 8753-8758.
83. Khan S.H. and O'Neill R.A. (eds) (1996) Modern Methods in Carbohydrate Chemistry, Harwood Academic, Amsterdam.
84. Pozsgay, V. (2000) Carbohydrates in Chemistry and Biology, vol 1, (eds B. Ernst, G.W. Hart and P. Sinay),Wiley-VCH Verlag GmbH, Weinheim, pp. 319-343.
85. Crich, D. (2002) Journal of Carbohydrate Chemistry, 21, 667-690.
86. El Ashry, E.S.H., Rashed, N. and Ibrahim, E.S.I. (2005) Current Organic Synthesis, 2, 175-213.
87. Huchel, U. and Schmidt, R.R. (1998) Tetrahedron Letters, 39, 7693-7694.
88. Muller, M., Huchel, U., Geyer, A. and Schmidt, R.R. (1999) The Journal of Organic Chemistry, 64, 6190-6201.
89. Muller, M. and Schmidt, R.R. (2001) European Journal of Organic Chemistry, 2055-2066.
90. Hanessian, S. and Lou, B. (2000) Chemical Reviews, 100, 4443-4463.
91. Hanessian, S., Ugolini, A., Dube, D., Hodges, P.J. and Andre, C. (1986) Journal of the American Chemical Society, 108, 2776-2778.
92. Woodward, R.B., Logusch, E., Nambiar, K.P., Sakan, K., Ward, D.E., Au-Yeung, B. W., Balaram, P., Browne, L.J., Card, P.J. and Chen, C.H. (1981) Journal of the American Chemical Society, 103, 3215-3217.
93. Tatsuta, K., Kobayashi, Y. and Gunji, H. (1988) The Journal of Antibiotics, 41, 1520-1523.
94. Tatsuta, K., Kobayashi, Y., Gunji, H., Masuda, H. and Kohoku, H. (1988) Tetrahedron Letters, 29, 3975-3978.
95. Toshima, K., Mukaiyama, S., Yoshida, T., Tamai, T. and Tatsuta, K. (1991) Tetrahedron Letters, 32, 6155-6158.
96. Hergenrother, P.J., Hodgson, A., Judd, A. S., Lee, W.-C. and Martin, S.F. (2003) Angewandte Chemie (International Edition), 42, 3278-3281.
97. Ravi, D., Kulkarni, V.R. and Mereyala, H. B. (1989) Tetrahedron Letters, 30, 4287-4290.
98. Mereyala, H.B. and Ravi, D. (1991) Tetrahedron Letters, 32, 7317-7320.
99. Mereyala, H.B., Hotha, S. and Gurjar, M.K. (1998) Chemical Communications, 685-686.
100. Mereyala, H.B. and Gurijala, V.R. (1993) Carbohydrate Research, 242, 277-280.
101. Mereyala, H.B., Gurrala, S.R. and Gadikota, R.R. (1997) Journal of the Chemical Society Perkin Transactions, 1, 3179-3182.
102. Chen, Q. and Kong, F. (1995) Carbohydrate Research, 272, 149-157.
103. Ning, J., Xing, Y. and Kong, F. (2003) Carbohydrate Research, 338, 55-60.
104. Pastuch, G., and Wandzik, I. and Szeja, W. (2000) Tetrahedron Letters, 41, 9923-9926.
105. Niemiec-Cyganek, A. and Szeja, W. (2003) Polish Journal of Chemistry, 77, 969-973.
106. Bogusiak, J. and Szeja, W. (1996) Carbohydrate Research, 295, 235-243.
107. Bogusiak, J. and Szeja, W. (1997) Synlett, 661-662.
108. Bogusiak, J. and Szeja, W. (2001) Carbohydrate Research, 330, 141-144.
109. Bogusiak, J. and Szeja, W. (2001) Tetrahedron Letters, 42, 141-144.
110. Kochetkov, N.K., Klimov, E.M., Malysheva, N.N. and Demchenko, A.V. (1993) Carbohydrate Research 242, C7-C10.
111. Kochetkov, N.K., Klimov, E.M., Malysheva, N.N. and Demchenko, A.V. (1989) Tetrahedron Letters, 30, 5499-5462.
112. Kochetkov, N.K., Klimov, E.M., Malysheva, N.N. and Demchenko, A.V. (1990) Bioorganicheskaia Khimiia, 16, 701-710.
113. Michalska, M., Orlich-Krezel, I. and Michalski, J. (1978) Tetrahedron, 34, 617-622.
114. Kudelska, W. and Michalska, M. (1994) Tetrahedron Letters, 40, 7459-7462.
115. Kudelska, W. and Michalska, M. (1995) Synthesis, 1539-1544.
116. Szeja, W. and Bogusiak, J. (1987) Carbohydrate Research, 170, 235-239.
117. Szeja, W. and Bogusiak, J. (1988) Synthesis, 224-226.
118. Laupichler, L., Sajus, H. and Thiem, J. (1992) Synthesis, 1133-1136.
119. Borowiecka, J. and Michalska, M. (1979) Carbohydrate Research, 86, C8-C10.
120. Borowiecka, J., Lipka, P. and Michalska, M. (1988) Tetrahedron, 44, 2067-2076.
121. Plante, O.J., Palmacci, E.R., Andrade, R. B. and Seeberger, P.H. (2001) Journal of the American Chemical Society, 123, 9545-9554.
122. Bielawska, H. and Michalska, M. (1991) Journal of Carbohydrate Chemistry, 10, 107-112.