Synthesis of peptides and oligosaccharides by using a recyclable fluorous tag

Tetrahedron Letters

Volumn 46, Issue 48, 2005, Pages 8293-8297

  Goto, Kohtaro ^a   Miura, Tsuyoshi ^a   Mizuno, Mamoru ^a  

^a NOGUCHI INSTITUTE   (Japan)

Author keywords

Fluorous; Oligosaccharide; Peptide; Recylce

Indexed keywords

ALCOHOL; OLIGOSACCHARIDE; PEPTIDE DERIVATIVE;

ARTICLE; CARBOHYDRATE SYNTHESIS; CHEMICAL REACTION; HYDROGENATION; PEPTIDE SYNTHESIS; RECYCLING;

EID: 27644595571     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.09.160     Document Type: Article

References (44)

1. I.T. Horváth, and J. Rábai Science 266 1994 72
2. X. Hao, O. Yamazaki, A. Yoshida, and J. Nishikido Tetrahedron Lett. 44 2003 4977
3. D. Crich, and S. Neelamkavil J. Am. Chem. Soc. 123 2001 7449
4. K.S.A. Vallin, Q. Zhang, M. Larhed, D.P. Curran, and A. Hallberg J. Org. Chem. 68 2003 6639
5. J. Moineau, G. Pozzi, S. Quici, and D. Sinou Tetrahedron Lett. 40 1999 7683
6. D. Chen, F. Qing, and Y. Huang Org. Lett. 4 2002 1003
7. S. Dandapani, and D.P. Curran Tetrahedron 58 2002 3855
8. A.P. Dobbs, and C. McGregor-Johnson Tetrahedron Lett. 43 2002 2807
9. 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
10. M.W. Markowicz, and R. Dembinski Org. Lett. 4 2002 3785
11. A.G.M. Barrett, D. Braddock, C.D. Catterick, D. Chadwick, J.P. Heschke, and R.M. McKinnell Synlett 2000 847
12. J.A. Gladysz D. Curran I.T. Horváh Handbook of Fluorous Chemistry 2004 VCH-Wiley Weinheim
13. A. Studer, S. Hadida, R. Ferritto, S.-Y. Kim, P. Jeger, P. Wipf, and D.P. Curran Science 275 1997 823
14. T. Miura, Y. Hirose, M. Ohmae, and T. Inazu Org. Lett. 3 2001 3947
15. T. Miura, and T. Inazu Tetrahedron Lett. 44 2003 1819
16. T. Miura, K. Goto, D. Hosaka, and T. Inazu Angew. Chem., Int. Ed. 42 2003 2047
17. K. Goto, T. Miura, D. Hosaka, H. Matsumoto, M. Mizuno, H. Ishida, and T. Inazu Tetrahedron 60 2004 8845
18. T. Miura, K. Goto, H. Waragai, H. Matsumoto, M. Ohmae, H. Ishida, A. Satoh, and T. Inazu J. Org. Chem. 69 2004 5348
19. T. Miura, S. Tsujino, A. Satoh, K. Goto, M. Mizono, M. Noguchi, T. Kajimoto, M. Node, Y. Murakami, N. Imai, and T. Inazu Tetrahedron 61 2005 6518
20. T. Miura, A. Satoh, K. Goto, Y. Murakami, N. Imai, and T. Inazu Tetrahedron: Asymmetry 16 2005 3
21. M. Mizuno, K. Goto, T. Miura, D. Hosaka, and T. Inazu Chem. Commun. 2003 972
22. M. Mizuno, K. Goto, T. Miura, T. Matsuura, and T. Inazu Tetrahedron Lett. 45 2004 3425
23. K. Goto, T. Miura, M. Mizuno, H. Takaki, N. Imai, Y. Murakami, and T. Inazu Synlett 2004 2221
24. M. Mizuno, K. Goto, and T. Miura Chem. Lett. 34 2005 426
25. 14) isomers and is called Fluorinert™ FC-72.
26. +: 3199.26. Found: 3199.28.
27. The product mixtures containing the fluorous compounds 5-6, 8-10, 13, and 16 were partitioned between FC-72 and MeCN. Compounds 15 and 17 were partitioned between FC-72 and MeOH. None of the fluorous compounds was detected by TLC of the organic layer after three extractions with FC-72, showing that they were quantitatively extracted into the FC-72 layer.
28. L.A. Carpino, and G.Y. Han J. Am. Chem. Soc. 92 1970 5748
29. G.B. Fields, and R.L. Noble Int. J. Peptide Protein Res. 31 1990 6991
30. 9 is a commercially available fluorocarbon solvent called Novec™ HFE-7200 (3M, Tokyo) that is miscible in common organic solvents and fluorous solvents.
31. +: 404.1969. Found: 404.1990.
32. B. Raju, and T. Kogan Tetrahedron Lett. 38 1997 4965
33. B. Dörner P. White Handbook of Solid Phase Synthesis 2002 E. Merck Darmstadt 38 39
34. HMPB; 4-(4-Hydroxymethyl-3-methoxyphenyloxy)-butanoyl.
35. M. Ueki, and T. Inazu Chem. Lett. 1982 45
36. M. Mizuno, K. Haneda, R. Iguchi, I. Muramoto, T. Kawakami, S. Aimoto, K. Yamamoto, and T. Inazu J. Am. Chem. Soc. 121 1999 284
37. +: 359.1602. Found: 359.1600.
38. Unpublished work.
39. +: 3390.32. Found: 3392.72.
40. G.H. Veeneman, S.H. Van Leeuwen, and J.H. Van Boom Tetrahedron Lett. 31 1990 1331
41. C. Gioeli, and J.B. Chattopadhyaya J. Chem. Soc., Chem. Commun. 1982 672
42. +: 1110.5. Found: 1110.9.
43. The β-isomer of 19 (i.e., gentiobiose) was not detected by NMR spectroscopic analysis.
44. +: 365.1054. Found: 365.1068.