Chinese Journal of Organic Chemistry >
Progress in the Chemical Synthesis of 2-Deoxy-glycosides
Received date: 2012-02-04
Revised date: 2012-04-20
Online published: 2012-05-21
Supported by
Project supported by the National Natural Science Foundation of China (Nos. 81072525, 21002014), the Research Fund for the Doctoral Program of Higher Education of China (No. 20100071120051), and the Fundamental Research Funds for the Central Universities (No. 10FX061).
2-Deoxy-glycosides are monosaccharides in which the hydroxyl group at C-2 is replaced with a hydrogen atom. They exist widely in natural products and show various bioactivity. The recent advances in organic synthesis of 2-deoxy-glycosides are summarized mainly focusing on direct etherification, direct glycosidic bond formation, temporary protecting groups, synthesis from non-sugar and so on.
Key words： 2-deoxy-glycosides; oligosaccharides; chemosynthesis methodology
Li Zhongzhen , Ding Ning , Zhang Wei , Wang Peng , Li Ming , Li Yingxia . Progress in the Chemical Synthesis of 2-Deoxy-glycosides[J]. Chinese Journal of Organic Chemistry, 2012 , 32(10) : 1812 -1826 . DOI: 10.6023/cjoc1202041
[1]Kennedy, J. F.; White, C. A. Bioactive Carbohydrates in Chemistry, Biochemistry, and Biology, Ellis Horwood Publishers, Chichester, 1983.
[2](a) Ohta, T.; Hasegawa, M. J. Antibiot. 1992, 45, 1167.
(b) De Lederkremer, R. M.; Marino, C. Adv. Carbohydr. Chem. Biochem. 2008, 61, 143.
[3]Wang, H.-J.; Vghhetto, G.; Rich, A. Biochemistry1987, 26, 1152.
[4]Hayasaks, T.; Inoue, Y. Biochemistry 1969, 8, 2342.
[5]Weymouth-Wilson, A. C. Nat. Prod. Rep. 1997, 14, 99.
[6]Carmona, A. T.; Moreno-Vargas, A. J.; Robina, I. Curr. Org. Synth. 2008, 5, 33.
[7](a) Marzabadi, C. H.; Franck, R. W. Tetrahedron2000, 56, 8385.
(b) Hou, D.-J.; Todd, L. L. Carbohydr. Res. 2009, 344, 1911.
[8]Takeuchi, K.; Higuchi, S.; Mukaiyama, T. Chem. Lett. 1997, 969.
[9]Toshima, K.; Nagai, H.; Matsumura, S. Synlett 1999, 1420.
[10]Takaaki, J.; Naoki, M.; Yasumasa, O.; Shuichi, M.; Kazunobu T. Tetrahedron Lett. 1999, 40, 5023.
[11]Morris, W. J.; Shair, M. D. Org. Lett. 2009, 11, 9.
[12]Paul, S.; Jayaraman, N. Carbohydr. Res. 2007, 342, 1305.
[13]Park, J.; Boltje, T. J.; Boons, G. J. Org. Lett. 2008, 10, 4367.
[14]Tanaka, H.; Yoshizawa, A.; Takahaashi, T. Angew. Chem., Int. Ed. Engl. 2007, 46, 2505.
[15](a) Wuts, P. G. M.; Bigelow, S. S. J. Org. Chem. 1983, 48, 3489.
(b) Takeda, K.; Kaji, E.; Harigaya, Y. Synthesis 1996, 341.
[16]Mukaiyama, T.; Shisa, S. Chem. Lett. 1979, 487.
[17]Kihlberg, J. O.; Bundle, D. R. J. Org. Chem. 1990, 55, 2860.
[18](a) Ferrier, R. J.; Vethaviyasar, N. Carbohydr. Res. 1973, 27, 55. (b) Van Cleve, J. W. Carbohydr. Res. 1979, 70, 161.
(c) Tsai, T. Y. R.; Jin, H.; Wiesner, K. Can. J. Chem. 1984, 62, 1403.
[19](a) Sati, S.; Ogawa, T. Carbohydr. Res. 1986, 155, C6.
(b) Sati, S.; Ogawa, T. Tetrahedron Lett. 1988, 29, 4759.
(c) Sakai, K.; Ogawa, T. Tetrahedron Lett. 1990, 31, 3035.
[20](a) Nicolaou, K. C.; Papahatjis, S. P. J. Am. Chem. Soc. 1983, 105, 2430.
(b) Roush, W. R.; Lin, X.; Straub, J. A. J. Org. Chem. 1991, 56, 1649.
[21](a) Veeneman, G. H.; J. H.; van Boom, J. H. Tetrahedron Lett. 1990, 31, 275.
(b) Veeneman, G. H.; J. H.; van Boom, J. H. Tetrahedron Lett. 1990, 31, 1331.
(c) Konradsson, P.; H. J. H.; van Boom, J. Tetrahedron Lett. 1990, 31, 4313.
(d) Ehara, T.; Hasegawa, A. Carbohydr. Res. 1996, 281, 237.
[22](a) Ito, Y.; Ogawa, T. Tetrahedron Lett. 1988, 29, 1061.
(b) Fujita, S.; Ogawa, T. Carbohydr. Res. 1994, 263, 181.
[23](a) Lonn, H. Carbohydr. Res. 1985, 139, 105.
(b) Lonn, H. J. Carbohydr. Chem. 1987, 6, 301.
(c) Mereyala, H. B.; Reddy, G. B. Tetrahedron 1992, 48, 545.
[24]Paul, S.; Jayaraman, N. Carbohydr. Res. 2004, 339, 2197.
[25]Lu, Y. S.; Ye, X. S. Synlett 2010, 1519.
[26]Gildersleeve, J.; Smith, A.; Sakurai, K.; Raghavan, S.; Kahne, D. J. Am. Chem. Soc. 1999, 121, 6176.
[27]Li, H.; Chen, M.-J.; Zhao, K. Tetrahedron Lett. 1997, 38, 6143.
[28]Hideyuki, N.; Shuichi, M.; Kazunobu, T. Chem. Lett. 2002, 1100.
[29]Hashimoto, S.; Hayashi, M.; Noyori, R. Tetrahedron Lett. 1984, 25, 1379.
[30](a) Kreuzer, M.; Thiem, J. Carbohydr. Res. 1986, 149, 347.
(b) Junnemann, J.; Lundt, I.; Thiem, J. Liebigs Ann. Chem. 1991, 8, 759.
[31]Matsumoto, T.; Maeta, H; Suzuki, K; Tsuchihashi, G.Tetrahedron Lett. 1988, 29, 3567.
[32](a) Suzuki, K.; Maeta, H; Suzuki, T; Matsumoto, T. Tetrahedron Lett. 1989, 30, 6879.
(b) Nicolaou, K. C.; Caulfield, T. J; Kataoka, H; Stylianides N. A. J. Am. Chem. Soc. 1990, 112, 3693.
(c) Nicolaou, K. C; Hummel, C. W; Iwabuchi, Y. J. Am. Chem. Soc. 1992, 114, 3126.
[33]Schene, H.; Waldmann, H. Synthesis.1999, 1411.
[34]Kazunobu, T.; Ken-ichi, K.; Shuichi, M. Synlett 1999, 813.
[35]Banik, B. K; Samajdar, S.; Banik, I.; Zegrocka, O.; Becker, F.F. Heterocycles.2001, 55, 227.
[36](a) Danishefsky, S. J.; Roberge, J. Y. Pure Appl. Chem. 1995, 67, 1647.
(b) Boons, G. J. Tetrahedron 1996, 52, 1095.
[37]Halcomb, R. L.; Danishefsky, S. J. J. Am. Chem. Soc. 1989, 111, 6661.
[38]Mcclure, K. F.; Danishefsky, S. J. Science.1993, 260, 1307.
[39](a) Toshima, K.; Tatsuta, K; Kinoshita, M. Bull. Chem. Soc. Jpn. 1988, 61, 2369.
(b) Cornia, M; Casiraghi, G. J. Org. Chem. 1991, 56, 5468.
[40](a) Igarashi, K.; Honma, T; Imagawa, T. J. Org. Chem. 1970, 35, 610.
(b) Boullanger, P.; Descotes, G. Carbohydr. Res. 1976, 51, 55.
(c) Horton, D.; Priebe, W; Varela, O. J. Org. Chem. 1986, 51, 3479.
(d) Bellucci, G.; Lo Moro, G. Tetrahedron 1997, 53, 3417.
[41]Tatsuta, K.; Fujimoto, K; Kinoshita, M; Umezwa, D. Carbohydr. Res. 1977, 54, 85.
[42]Thiem, J.; Karl, H.; Schwentner, J. Synthesis 1978, 696.
[43](a) Preuss, R.; Schmidt, R. Synthesis 1988, 694.
(b) Roush, W. R.; Sebesta, D. P.; Bennett, C. E. Tetrahedron 1997, 53, 8825.
(c) Grewal, G; Kaila, N; Franck, R. W. J. Org. Chem. 1992, 57, 2084.
[44]Tiem, J.; Klaffke, W. J. Org. Chem. 1989, 54, 2006.
[45](a) Danishefsky, S. J.; Bilodeau, M. T. Angew. Chem.Int. Ed. Engl. 1996, 35, 1380.
(b) Gervay, J.; Danishefsky, S. J. J. Org. Chem. 1991, 56, 5448.
[46](a) Leblanc, Y.; Fitzsimmons, B. J.; Springer, J. P.; Rokach, J. J. Am. Chem. Soc. 1989, 111, 2995.
(b) Toepfer, A.; Schmidt, R. R. Carbohydr. Res. 1993, 247, 159.
(c) Capozzi, G.; Dios, A.; Tamarez, M. Angew. Chem. Int. Ed. Engl. 1996, 35, 777.
[47]Lin, H.-C.; Pan, J.-F.; Chen, Y.-B.; Lin, Z.-P.; Lin, C.-H. Tetrahedron. 2011, 67, 6362.
[48]Kim, K.-S.; Lee, Y.-J.; Kim, H.-Y.; Kang, S.-S.; Kwon, S.-Y. Org. Biomol. Chem. 2004, 2, 2408.
[49]Kim, K. S.; Park, J.; Lee, Y. J.; Seo, Y. S. Angew. Chem., Int. Ed. 2003, 42, 4459.
[50]Zhu, Y.-G.; Yu, B. Angew. Chem., Int. Ed. 2011, 50, 8329.
[51]Li, Y.; Yang, X.-Y.; Zhu, C.-S.; Yu, B.; Liu, Y.-P.; Yang, Y. Chem.-Eur. J. 2010, 16, 1871.
[52]Ma, Y.; Li, Z.; Shi, H.; Zhang, J.; Yu, B. J. Org. Chem. 2011, 76, 9748.
[53](a) Ogawa, T.; Beppu, K.; Nakabayashi, S. Carbohydr. Res. 1981, 93, C6.
(b) Mukaiyama, T.; Kobayashi, S. Chem. Lett. 1989, 145.
(c) Mukaiyama, T.; Aizawa, H. Chem. Lett. 1991, 533.
[54](a) Kimura, Y.; Suzuki, M.; Terashima, S. Chem. Lett. 1984, 501.
(b) Jutten, P.; Scharf, H. D.; Raabe, G. J. Org. Chem. 1991, 56, 7144.
[55]Ley, S. V.; Armstrong, A.; Williams, D. J.; Woods, M. J. Chem. Soc. Perkin Trans. 1 1991, 667.
[56](a) Tietze, L. F.; Fische, P.; Guder, H. J. Tetrahedron Lett. 1982, 23, 4661.
(b) Priebe, W.; Grynkiewicz, G; Neamati, N. Tetrahedron Lett. 1991, 32, 2079.
(c) Kolar, C.; Kneissl, G.; Knödler, U; Dhmel, K. Carbohydr. Res. 1991, 209, 89.
[57]Bucher, C.; Gilmour, R. Angew. Chem., Int. Ed. 2010, 49, 8724.
[58](a) Thiem, J.; Klaffke, W. Top. Curr. Chem. 1990, 154, 285.
(b) Bock, K.; Pedersen, C.; Thiem, J. Carbohydr. Res. 1979, 73, 85.
[59]Thiem, J.; Gerken, M; Schöttmer, B; Weigand, J. Carbohydr. Res. 1987, 164, 327.
[60]Rodriguez, M. A.; Boutureira, O.; Arnes, X.; Matheu, M. I.; Diaz, Y.; Castill髇, S. J. Org. Chem. 2005, 70, 10297.
[61]Boutureira, O.; Rodriguez, M. A.; Benito, D.; Matheu, M. I.; Diaz, Y.; Castill髇, S. Eur. J. Org. Chem. 2007, 3564.
[62]Nicolaou, K. C.; Ladduwahetty, T.; Randall, J. L.; Chucholowski, A. J. Am. Chem. Soc. 1986, 108, 2466.
[63]Nicolaou, K. C.; Helen, J.; Rodrfguez, R. M. Angew. Chem., Int. Ed. 2000, 39, 1089.
[64]Zuurmond, H. M.; van der Klein, P. A. M.; J. H.; van der Marel, G.A; van Boom, J. H. Tetrahedron 1993, 49, 6501.
[65]Toshima, K.; Mukaiyama, S.; Nozaki, Y.; Inokuchi, K.; Nakata, M.; Tatsuta, K. J. Am. Chem. Soc. 1994, 116, 9042.
[66](a) Yu, B.; Yang, Z.-Y. Org. Lett. 2001, 3, 377.
(b) Yu, B.; Yang, Z.-Y. Carbohydr. Res. 2001, 333, 105.
(c) Yu, B.; Yang, Z.-Y. Tetrahedron Lett. 2000, 41, 2961.
[67]Yu, B.; Wang, P. Org. Lett. 2002, 4, 1919.
[68]Hou, D.-J.; Lowary, T. L. J. Org. Chem. 2009, 74, 2278.
[69]Lin, H.-C.; Du, W.-P.; Chang, C.-C; Lin, C.-H. Tetrahedron Lett. 2005, 46, 5071
[70](a) Zhou, M.; O'Doherty, G. A. Org. Lett. 2006, 8, 4339.
(b) Zhou, M.; O'Doherty, G. A. J. Org. Chem. 2007, 72, 2485McDonald, F. E; Reddy, K. S; Diaz, Y. J. Am. Chem. Soc. 2000, 122, 4304.
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