2-脱氧糖糖苷的化学合成进展
收稿日期: 2012-02-04
修回日期: 2012-04-20
网络出版日期: 2012-05-21
基金资助
国家自然科学基金(Nos. 81072525, 21002014)、教育部博士点新教师基金(No. 20100071120051)、中央高校专项基金(No. 10FX061)资助项目.
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).
李仲振 , 丁宁 , 张伟 , 王鹏 , 李明 , 李英霞 . 2-脱氧糖糖苷的化学合成进展[J]. 有机化学, 2012 , 32(10) : 1812 -1826 . DOI: 10.6023/cjoc1202041
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
[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.
/
〈 |
|
〉 |