Parallel synthesis of multi-branched oligosaccharides related to elicitor active pentasaccharide in rice cell based on orthogonal deprotection and glycosylation strategy

Tetrahedron Letters

Volumn 44, Issue 15, 2003, Pages 3053-3057

  Tanaka, Hiroshi ^a   Amaya, Toru ^a   Takahashi, Takashi ^a  

^a Tokyo Institute of Technology ^*  (Japan)

Author keywords

Automated synthesizer; Branched oligosaccharides; Combinatorial chemistry; Orthogonal deprotection; Phytoalexin elicitor

Indexed keywords

CARBOHYDRATE; OLIGOSACCHARIDE; PENTASACCHARIDE;

ARTICLE; CARBOHYDRATE ANALYSIS; CARBOHYDRATE SYNTHESIS; CHEMICAL REACTION; DEPROTECTION REACTION; GLYCOSYLATION; HYDROGENOLYSIS; RICE;

STAPHYLOCOCCUS PHAGE 3A;

EID: 0037424734     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00553-7     Document Type: Article

References (36)

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10. For synthetic studies of phytoalexin elicitors in soybeans, see: (a) Yamada, H.; Harada, T.; Takahashi, T. J. Am. Chem. Soc. 1994, 116, 7919-7920; (b) Yamada, H.; Takimoto, H.; Ikeda, T.; Tsukamoto, H.; Harada, T.; Takahashi, T. Synlett 2001, 1751-1754; (c) Tanaka, H.; Adachi, M.; Tsukamoto, H.; Ikeda, T.; Yamada, H.; Takahashi, T. Org. Lett. 2002, 4, 4213-4216.
11. For synthetic studies of phytoalexin elicitors in soybeans, see: (a) Yamada, H.; Harada, T.; Takahashi, T. J. Am. Chem. Soc. 1994, 116, 7919-7920; (b) Yamada, H.; Takimoto, H.; Ikeda, T.; Tsukamoto, H.; Harada, T.; Takahashi, T. Synlett 2001, 1751-1754; (c) Tanaka, H.; Adachi, M.; Tsukamoto, H.; Ikeda, T.; Yamada, H.; Takahashi, T. Org. Lett. 2002, 4, 4213-4216.
12. For synthetic studies of phytoalexin elicitors in rice, see: (a) Amaya, T.; Tanaka, H.; Yamaguchi, T.; Shibuya, N.; Takahashi, T. Tetrahedron Lett. 2001, 42, 9191-9194; (b) Takahashi, T.; Okano, A.; Amaya, T.; Tanaka, H.; Doi, T. Synlett 2002, 911-914.
13. For synthetic studies of phytoalexin elicitors in rice, see: (a) Amaya, T.; Tanaka, H.; Yamaguchi, T.; Shibuya, N.; Takahashi, T. Tetrahedron Lett. 2001, 42, 9191-9194; (b) Takahashi, T.; Okano, A.; Amaya, T.; Tanaka, H.; Doi, T. Synlett 2002, 911-914.
14. For orthogonal deprotection strategy on a mono-saccharide scaffold, see: (a) Wunberg, T.; Kallus, C.; Opatz, T.; Henke, S.; Schmidt, W.; Kunz, H. Angew. Chem., Int. Ed. 1998, 37, 2503-2505; (b) Wong, C.-H.; Ye, X.-S.; Zhang, Z. J. Am. Chem. Soc. 1998, 120, 7137-7138; (c) Kallus, C.; Opatz, T.; Wunberg, T.; Schmidt, W.; Henke, S.; Kunz, H. Tetrahedron Lett. 1999, 40, 7783-7786; (d) Zhu, T.; Boons, G.-J. Tetrahedron: Asymmetry 2000, 11, 199-205.
15. For orthogonal deprotection strategy on a mono-saccharide scaffold, see: (a) Wunberg, T.; Kallus, C.; Opatz, T.; Henke, S.; Schmidt, W.; Kunz, H. Angew. Chem., Int. Ed. 1998, 37, 2503-2505; (b) Wong, C.-H.; Ye, X.-S.; Zhang, Z. J. Am. Chem. Soc. 1998, 120, 7137-7138; (c) Kallus, C.; Opatz, T.; Wunberg, T.; Schmidt, W.; Henke, S.; Kunz, H. Tetrahedron Lett. 1999, 40, 7783-7786; (d) Zhu, T.; Boons, G.-J. Tetrahedron: Asymmetry 2000, 11, 199-205.
16. For orthogonal deprotection strategy on a mono-saccharide scaffold, see: (a) Wunberg, T.; Kallus, C.; Opatz, T.; Henke, S.; Schmidt, W.; Kunz, H. Angew. Chem., Int. Ed. 1998, 37, 2503-2505; (b) Wong, C.-H.; Ye, X.-S.; Zhang, Z. J. Am. Chem. Soc. 1998, 120, 7137-7138; (c) Kallus, C.; Opatz, T.; Wunberg, T.; Schmidt, W.; Henke, S.; Kunz, H. Tetrahedron Lett. 1999, 40, 7783-7786; (d) Zhu, T.; Boons, G.-J. Tetrahedron: Asymmetry 2000, 11, 199-205.
17. For orthogonal deprotection strategy on a mono-saccharide scaffold, see: (a) Wunberg, T.; Kallus, C.; Opatz, T.; Henke, S.; Schmidt, W.; Kunz, H. Angew. Chem., Int. Ed. 1998, 37, 2503-2505; (b) Wong, C.-H.; Ye, X.-S.; Zhang, Z. J. Am. Chem. Soc. 1998, 120, 7137-7138; (c) Kallus, C.; Opatz, T.; Wunberg, T.; Schmidt, W.; Henke, S.; Kunz, H. Tetrahedron Lett. 1999, 40, 7783-7786; (d) Zhu, T.; Boons, G.-J. Tetrahedron: Asymmetry 2000, 11, 199-205.
18. The use of Alloc as a hydroxyl protecting group in oligosaccharide synthesis has been reported in a few examples. See: (a) Teshima, T.; Nakajima, K.; Takahashi, M.; Shiba, T. Tetrahedron Lett. 1992, 33, 363-366; (b) Harada, T.; Yamada, H.; Tsukamoto, H.; Takahashi, T. J. Carbohydr. Chem. 1995, 14, 165-170; (c) Depré, D.; Düffels, A.; Green, L. G.; Lenz, R.; Ley, S. V.; Wong, C.-H. Chem. Eur. J. 1999, 5, 3326-3340; (d) Adinolfi, M.; Barone, G.; Guariniello, L.; Iadonisi, A. Tetrahedron Lett. 2000, 41, 9305-9309.
19. The use of Alloc as a hydroxyl protecting group in oligosaccharide synthesis has been reported in a few examples. See: (a) Teshima, T.; Nakajima, K.; Takahashi, M.; Shiba, T. Tetrahedron Lett. 1992, 33, 363-366; (b) Harada, T.; Yamada, H.; Tsukamoto, H.; Takahashi, T. J. Carbohydr. Chem. 1995, 14, 165-170; (c) Depré, D.; Düffels, A.; Green, L. G.; Lenz, R.; Ley, S. V.; Wong, C.-H. Chem. Eur. J. 1999, 5, 3326-3340; (d) Adinolfi, M.; Barone, G.; Guariniello, L.; Iadonisi, A. Tetrahedron Lett. 2000, 41, 9305-9309.
20. The use of Alloc as a hydroxyl protecting group in oligosaccharide synthesis has been reported in a few examples. See: (a) Teshima, T.; Nakajima, K.; Takahashi, M.; Shiba, T. Tetrahedron Lett. 1992, 33, 363-366; (b) Harada, T.; Yamada, H.; Tsukamoto, H.; Takahashi, T. J. Carbohydr. Chem. 1995, 14, 165-170; (c) Depré, D.; Düffels, A.; Green, L. G.; Lenz, R.; Ley, S. V.; Wong, C.-H. Chem. Eur. J. 1999, 5, 3326-3340; (d) Adinolfi, M.; Barone, G.; Guariniello, L.; Iadonisi, A. Tetrahedron Lett. 2000, 41, 9305-9309.
21. The use of Alloc as a hydroxyl protecting group in oligosaccharide synthesis has been reported in a few examples. See: (a) Teshima, T.; Nakajima, K.; Takahashi, M.; Shiba, T. Tetrahedron Lett. 1992, 33, 363-366; (b) Harada, T.; Yamada, H.; Tsukamoto, H.; Takahashi, T. J. Carbohydr. Chem. 1995, 14, 165-170; (c) Depré, D.; Düffels, A.; Green, L. G.; Lenz, R.; Ley, S. V.; Wong, C.-H. Chem. Eur. J. 1999, 5, 3326-3340; (d) Adinolfi, M.; Barone, G.; Guariniello, L.; Iadonisi, A. Tetrahedron Lett. 2000, 41, 9305-9309.
22. The use of Fmoc as a hydroxyl protecting group in oligosaccharide synthesis has been reported in a few examples. See: (a) Freese, S. J.; Vann, W. F. Carbohydr. Res. 1996, 281, 313-319; (b) Nicolaou, K. C.; Winssinger, N.; Pastor, J.; DeRoose, F. J. Am. Chem. Soc. 1997, 119, 449-450; (c) Nicolaou, K. C.; Watanabe, N.; Li, J.; Pastor, J.; Winssinger, N. Angew. Chem., Int. Ed. 1998, 37, 1559-1561; (d) Roussel, F.; Knerr, L.; Grathwohl, M.; Schmidt, R. R. Org. Lett. 2000, 2, 3043-3046; (e) Zhu, T.; Boons, G.-J. J. Am. Chem. Soc. 2000, 122, 10222-10223; (f) Wu, X.; Grathwohl, M.; Schmidt, R. R. Org. Lett. 2001, 3, 747-750.
23. The use of Fmoc as a hydroxyl protecting group in oligosaccharide synthesis has been reported in a few examples. See: (a) Freese, S. J.; Vann, W. F. Carbohydr. Res. 1996, 281, 313-319; (b) Nicolaou, K. C.; Winssinger, N.; Pastor, J.; DeRoose, F. J. Am. Chem. Soc. 1997, 119, 449-450; (c) Nicolaou, K. C.; Watanabe, N.; Li, J.; Pastor, J.; Winssinger, N. Angew. Chem., Int. Ed. 1998, 37, 1559-1561; (d) Roussel, F.; Knerr, L.; Grathwohl, M.; Schmidt, R. R. Org. Lett. 2000, 2, 3043-3046; (e) Zhu, T.; Boons, G.-J. J. Am. Chem. Soc. 2000, 122, 10222-10223; (f) Wu, X.; Grathwohl, M.; Schmidt, R. R. Org. Lett. 2001, 3, 747-750.
24. The use of Fmoc as a hydroxyl protecting group in oligosaccharide synthesis has been reported in a few examples. See: (a) Freese, S. J.; Vann, W. F. Carbohydr. Res. 1996, 281, 313-319; (b) Nicolaou, K. C.; Winssinger, N.; Pastor, J.; DeRoose, F. J. Am. Chem. Soc. 1997, 119, 449-450; (c) Nicolaou, K. C.; Watanabe, N.; Li, J.; Pastor, J.; Winssinger, N. Angew. Chem., Int. Ed. 1998, 37, 1559-1561; (d) Roussel, F.; Knerr, L.; Grathwohl, M.; Schmidt, R. R. Org. Lett. 2000, 2, 3043-3046; (e) Zhu, T.; Boons, G.-J. J. Am. Chem. Soc. 2000, 122, 10222-10223; (f) Wu, X.; Grathwohl, M.; Schmidt, R. R. Org. Lett. 2001, 3, 747-750.
25. The use of Fmoc as a hydroxyl protecting group in oligosaccharide synthesis has been reported in a few examples. See: (a) Freese, S. J.; Vann, W. F. Carbohydr. Res. 1996, 281, 313-319; (b) Nicolaou, K. C.; Winssinger, N.; Pastor, J.; DeRoose, F. J. Am. Chem. Soc. 1997, 119, 449-450; (c) Nicolaou, K. C.; Watanabe, N.; Li, J.; Pastor, J.; Winssinger, N. Angew. Chem., Int. Ed. 1998, 37, 1559-1561; (d) Roussel, F.; Knerr, L.; Grathwohl, M.; Schmidt, R. R. Org. Lett. 2000, 2, 3043-3046; (e) Zhu, T.; Boons, G.-J. J. Am. Chem. Soc. 2000, 122, 10222-10223; (f) Wu, X.; Grathwohl, M.; Schmidt, R. R. Org. Lett. 2001, 3, 747-750.
26. The use of Fmoc as a hydroxyl protecting group in oligosaccharide synthesis has been reported in a few examples. See: (a) Freese, S. J.; Vann, W. F. Carbohydr. Res. 1996, 281, 313-319; (b) Nicolaou, K. C.; Winssinger, N.; Pastor, J.; DeRoose, F. J. Am. Chem. Soc. 1997, 119, 449-450; (c) Nicolaou, K. C.; Watanabe, N.; Li, J.; Pastor, J.; Winssinger, N. Angew. Chem., Int. Ed. 1998, 37, 1559-1561; (d) Roussel, F.; Knerr, L.; Grathwohl, M.; Schmidt, R. R. Org. Lett. 2000, 2, 3043-3046; (e) Zhu, T.; Boons, G.-J. J. Am. Chem. Soc. 2000, 122, 10222-10223; (f) Wu, X.; Grathwohl, M.; Schmidt, R. R. Org. Lett. 2001, 3, 747-750.
27. The use of Fmoc as a hydroxyl protecting group in oligosaccharide synthesis has been reported in a few examples. See: (a) Freese, S. J.; Vann, W. F. Carbohydr. Res. 1996, 281, 313-319; (b) Nicolaou, K. C.; Winssinger, N.; Pastor, J.; DeRoose, F. J. Am. Chem. Soc. 1997, 119, 449-450; (c) Nicolaou, K. C.; Watanabe, N.; Li, J.; Pastor, J.; Winssinger, N. Angew. Chem., Int. Ed. 1998, 37, 1559-1561; (d) Roussel, F.; Knerr, L.; Grathwohl, M.; Schmidt, R. R. Org. Lett. 2000, 2, 3043-3046; (e) Zhu, T.; Boons, G.-J. J. Am. Chem. Soc. 2000, 122, 10222-10223; (f) Wu, X.; Grathwohl, M.; Schmidt, R. R. Org. Lett. 2001, 3, 747-750.
28. Green T.W., Wuts P.G.M. Protective Groups in Organic Synthesis. 3rd ed. 1999;168 John Wiley & Sons, New York.
29. 31Si: C, 68.54; H, 5.90. Found: C, 65.55; H, 6.01%.
30. Kunz H., Unverzagt C. Angew. Chem., Int. Ed. Engl. 23:1984;436-437.
31. 4 (5 mg, 4.3 μmol) in THF (0.2 mL) were added to each of the reaction vessels 1-4 at room temperature. The reaction mixtures were stirred at the same temperature for 15 min. For removal of the Fmoc group, a solution of piperidine (20 μL, 0.20 mmol) in THF (0.2 mL) was added to each of the reaction vessels 2, 3, 5, and 6 at room temperature. The reaction mixtures were stirred at the same temperature for 15 min. For removal of the Lev group, a solution of hydrazine (29 μL, 0.93 mmol)-acetic acid (73 μL, 1.28 mmol) in THF (0.2 mL) was added to each of the reaction vessels 3, 4, 6, and 7 at the same temperature. After stirring at the same temperature for 30 min, the reaction mixtures were automatically subjected to flash chromatography in parallel fashion, eluting with hexane: ethyl acetate (1: 4) to give the seven tetrasaccharides 4a (26.4 mg, 0.013 mmol, 79% yield), 4b (26.3 mg, 0.014 mmol, 79% yield), 4c (25.8 mg, 0.014 mmol, 83% yield), 4d (24.4 mg, 0.014 mmol, 83% yield), 4e (22.7 mg, 0.013 mmol, 76% yield) 4f (24.4 mg, 0.013 mmol, 77% yield), 4g (24.0 mg, 0.015 mmol, 85% yield), respectively.
32. L-COS™ is purchased from Moritex Corporation, Japan.
33. Combi Flash™ automated column chromatograph with ten parallel columns is purchased from Isco, Incorporation.
34. +): 1170.4147, found 1170.4194.
35. 13C NMR, and MS) of pentaglycosides 3a and 3b were identical with those of our previous reported authentic samples, see Ref. 5a.
36. Agrawal P.K. Phytochemistry. 31:1992;3307-3330.