Rapid oligosaccharide synthesis on a fluorous support

Tetrahedron

Volumn 60, Issue 40, 2004, Pages 8845-8854

  Goto, Kohtaro ^a   Miura, Tsuyoshi ^a   Hosaka, Daisuke ^a   Matsumoto, Hiroharu ^a   Mizuno, Mamoru ^a   Ishida, Hide Ki ^a   Inazu, Toshiyuki ^a,b  

^a NOGUCHI INSTITUTE   (Japan)

^b TOKAI UNIVERSITY   (Japan)

Author keywords

Fluorous; Glycosylation; Oligosaccharide; Support; Synthetic method

Indexed keywords

OLIGOSACCHARIDE; ORGANIC SOLVENT;

ARTICLE; CARBOHYDRATE ANALYSIS; CARBOHYDRATE SYNTHESIS; CHEMICAL REACTION; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS; THIN LAYER CHROMATOGRAPHY;

EID: 4444234077     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.07.027     Document Type: Article

References (71)

1. A. Varki Glycobiology 3 1993 97
2. R.A. Dwek Chem. Rev. 96 1996 683
3. D.L. Blithe Trends Glycosci. Glycotechnol. 5 1993 81
4. S. Manabe, and Y. Ito J. Am. Chem. Soc. 124 2002 12638
5. H. Ando, S. Manabe, Y. Nakahara, and Y. Ito J. Am. Chem. Soc. 123 2001 3848
6. O.J. Plante, E.R. Palmacci, and P.H. Seeberger Science 291 2001 1523
7. E. Eichler, F. Yan, J. Sealy, and D.M. Whitfield Tetrahedron 57 2001 6679
8. Y. Ito, O. Kanie, and T. Ogawa Angew. Chem., Int. Ed. Engl. 35 1996 2510
9. S.P. Douglas, D.M. Whitfield, and J.J. Krepinsky J. Am. Chem. Soc. 117 1995 2116 and references cited therein
10. I.T. Horváth, and J. Rábai Science 266 1994 72
11. C.C. Tzschucke, C. Markert, W. Bannwarth, S. Roller, A. Hebel, and R. Haag Angew. Chem., Int. Ed. 41 2002 3964
12. J. Nishikido, M. Kamishima, H. Matsuzawa, and K. Mikami Tetrahedron 58 2002 8345
13. C. Rocaboy, and J.A. Gladysz Org. Lett. 4 2002 1993
14. Y. Nakamura, S. Takeuchi, K. Okumura, and Y. Ohga Tetrahedron 57 2001 5565
15. A.G.M. Barrett, D.C. Braddock, D. Catterick, D. Chadwick, J.P. Henschke, and R.M. McKinnell Synlett 2000 847
16. I.T. Horváth Acc. Chem. Res. 31 1998 641 and references cited therein
17. Q. Zhang, Z. Luo, and D.P. Curran J. Org. Chem. 65 2000 8866
18. D.P. Curran Pure Appl. Chem. 72 2000 1649
19. D.P. Curran Angew. Chem., Int. Ed. 37 1998 1174 and references cited therein
20. X. Hao, O. Yamazaki, A. Yoshida, and J. Nishikido Tetrahedron Lett. 44 2003 4977
21. D. Crich, and S. Neelamkavil J. Am. Chem. Soc. 123 2001 7449
22. K.S.A. Vallin, Q. Zhang, M. Larhed, D.P. Curran, and A. Hallberg J. Org. Chem. 68 2003 6639
23. J. Moineau, G. Pozzi, S. Quici, and D. Sinou Tetrahedron Lett. 40 1999 7683
24. D. Chen, F. Qing, and Y. Huang Org. Lett. 4 2002 1003
25. S. Dandapani, and D.P. Curran Tetrahedron Lett. 58 2002 3855
26. A.P. Dobbs, and C. McGregor-Johnson Tetrahedron Lett. 43 2002 2807
27. J. Rábai, D. Szabó, E.K. Borbás, I. Kövesi, I. Kövesdi, A. Csàmpai, A. Gömöry, V.E. Pashinnik, and Y.G. Shermolovich J. Fluorine Chem. 114 2002 199
28. M.W. Markowicz, and R. Dembinski Org. Lett. 4 2002 3785
29. A.G.M. Barrett, D. Braddock, C.D. Catterick, D. Chadwick, J.P. Heschke, and R.M. McKinnell Synlett 2000 847
30. C.C. Tzschucke, C. Markert, H. Glatz, and W. Bannwarth Angew. Chem., Int. Ed. 41 2002 4500
31. C. Markert, and W. Bannwarth Helv. Chim. Acta 85 2002 1887
32. M. Hoshino, P. Degenkolb, and D.P. Curran J. Org. Chem. 62 1997 8341
33. D.P. Curran, and M. Hoshino J. Org. Chem. 61 1996 6480
34. W. Zhang, Z. Luo, C.H. Chen, and D.P. Curran J. Am. Chem. Soc. 124 2002 10443
35. D.P. Curran, and T. Furukawa Org. Lett. 4 2002 2233
36. Q. Zhang, A. Rivkin, and D.P. Curran J. Am. Chem. Soc. 124 2002 5774
37. D.P. Curran Synlett 2001 1488
38. Z. Luo, Q. Zhang, Y. Oderaotoshi, and D.P. Curran Science 291 2001 1766
39. L. Manzoni Chem. Commun. 2003 2930
40. P. Wipf, J.T. Reeves, R. Balachandran, K.A. Giuliano, E. Hamel, and B.W. Day J. Am. Chem. Soc. 122 2000 9391
41. S. Röver, and P. Wipf Tetrahedron Lett. 40 1999 5667
42. P. Wipf, and J.T. Reeves Tetrahedron Lett. 40 1999 5139
43. P. Wipf, and J.T. Reeves Tetrahedron Lett. 40 1999 4649
44. A. Studer, and D.P. Curran Tetrahedron 53 1997 6681
45. D.P. Curran, R. Ferritto, and Y. Hua Tetrahedron Lett. 39 1998 4937
46. D.P. Curran, M. Amatore, D. Guthrie, M. Campbell, E. Go, and J.Z. Luo J. Org. Chem. 68 2003 4643
47. D. Schwinn, and W. Bannwarth Helv. Chim. Acta 85 2002 255
48. D.V. Filippov, J.D. Zoelen, S.P. Oldfield, G.A. Marel, H.S. Overkleeft, J.W. Drijfhout, and J.H. Boom Tetrahedron Lett. 43 2002 7809
49. J. Pardo, A. Cobas, E. Guitlán, and L. Castedo Org. Lett. 3 2001 3711
50. Z. Luo, J. Williams, R.W. Read, and D.P. Curran J. Org. Chem. 66 2001 4261
51. T. Miura, Y. Hirose, M. Ohmae, and T. Inazu Org. Lett. 3 2001 3947
52. T. Miura, and T. Inazu Tetrahedron Lett. 44 2003 1819
53. T. Miura, K. Goto, D. Hosaka, and T. Inazu Angew. Chem., Int. Ed. 42 2003 2047
54. E. Zang, and P.J. Sadler Synth. Commun. 27 18 1997 3145
55. Schmidt method: R.R. Schmidt, J. Michel, and M. Roos Liebigs Ann. Chem. 1984 1343
56. The product mixtures containing the fluorous compounds 13, 16 and 24 were partitioned between FC-72 and MeOH. Those containing the fluorous compound 14 and 22 were partitioned FC-72, toluene and water. The product containing the fluorous compound 21 was partitioned between FC-72 and acetonitrile. None of the fluorous compounds were detected by TLC of the organic layer after three times extraction with FC-72, which shows that these compounds were quantitatively extracted with FC-72.
57. 9 is a commercially available fluorocarbon solvent (3 M, Tokyo), which is called Novec™ HFE-7200.
58. 14) isomers and is called Fluorinert™ FC-72.
59. The anomer ratio of compound 19 (the newly formed anomeric position) was determined to be α/β=60:40 by NMR spectroscopic analysis. Moreover, the correlation between anomeric protons of galactose residue and 6-position carbons of glucose residue of the compound 19 was observed by HMQC and HMBC of NMR spectroscopic analysis.
60. Compound 19 was identified by comparison of spectroscopic data of the authentic samples (melibiose and arolactose).
61. W. Xu, S.A. Springfield, and J.T. Koh Carbohydr. Res. 325 2000 169
62. The starting materials 14 and 22 were not observed by TLC after the glycosylation.
63. The anomer ratio of compound 26 (the newly formed anomeric position) was determined to be α/β=78:22 based on NMR spectroscopic analysis. The glycoside linkages of compound 26 were analyzed using the above NMR spectroscopic analysis in Ref. 25.
64. Compound 26 was identified by comparison of spectroscopic data of an authentic sample: S. Koto, N. Morishima, S. Shichi, H. Haigoh, M. Hirooka, M. Okamoto, T. Higuchi, K. Shimizu, Y. Hashimoto, T. Irisawa, H. Kawasaki, Y. Takahashi, M. Yamazaki, Y. Mori, K. Kudo, T. Ikegaki, S. Suzuki, and S. Zen Bull. Chem. Soc. Jpn 65 1992 3257
65. G.H. Veeneman, S.H. Van Leeuwen, and J.H. Van Boom Tetrahedron Lett. 31 1990 1331
66. W. Köenigs, and E. Knurr Chemische Berichte 34 1901 957
67. T. Matsumoto, H. Maeta, K. Suzuki, and G. Tsuchihashi Tetrahedron Lett. 29 1988 3567
68. T. Matsumoto, H. Maeta, K. Suzuki, and G. Tsuchihashi Tetrahedron Lett. 29 1988 3571
69. T. Matsumoto, H. Maeta, K. Suzuki, and G. Tsuchihashi Tetrahedron Lett. 29 1988 3575
70. K. Suzuki, H. Maeta, and T. Matsumoto Tetrahedron Lett. 30 1989 4853
71. T. Mukaiyama, Y. Murai, and S. Shoda Chem. Lett. 1981 431