Simple formylacetal (CH2) as a novel linker for saccharide synthesis on soluble-polymer support

Tetrahedron Letters

Volumn 45, Issue 4, 2004, Pages 787-790

  Oikawa, Masato ^a,b   Tanaka, Tatsushi ^b   Kusumoto, Shoichi ^b   Sasaki, Makoto ^a  

^a TOHOKU UNIVERSITY   (Japan)

^b OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL DERIVATIVE; GLUCOSE; LEWIS ACID; MACROGOL; POLYMER; TRIFLUOROACETIC ACID;

ARTICLE; CARBOHYDRATE SYNTHESIS; CATALYST; CHEMICAL REACTION; GLYCOSYLATION; IMMOBILIZATION; MOLECULE; PURIFICATION; QUANTUM YIELD; SOLUBILITY;

EID: 0346787852     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.11.036     Document Type: Article

References (39)

1. Bayer E., Mutter M. Nature. 237:1972;512-513.
2. Gravert D.J., Janda K.D. Chem. Rev. 97:1997;489-509 Wentworth P., Janda K.D. Chem. Commun. 1999;1917-1924.
3. Gravert D.J., Janda K.D. Chem. Rev. 97:1997;489-509 Wentworth P., Janda K.D. Chem. Commun. 1999;1917-1924.
4. Ross A.J., Ivanova I.A., Higson A.P., Nikolaev A.V. Tetrahedron Lett. 41:2000;2449-2452.
5. Ito Y., Kanie O., Ogawa T. Angew. Chem., Int. Ed. 35:1996;2510-2512 Ito Y., Ogawa T.J. Am. Chem. Soc. 119:1997;5562-5566 Manabe S., Ito Y., Ogawa T. Synlett. 1998;628-630 Zhu T., Boons G.J. Tetrahedron: Asymmetry. 11:2000;199-205.
6. Ito Y., Kanie O., Ogawa T. Angew. Chem., Int. Ed. 35:1996;2510-2512 Ito Y., Ogawa T.J. Am. Chem. Soc. 119:1997;5562-5566 Manabe S., Ito Y., Ogawa T. Synlett. 1998;628-630 Zhu T., Boons G.J. Tetrahedron: Asymmetry. 11:2000;199-205.
7. Ito Y., Kanie O., Ogawa T. Angew. Chem., Int. Ed. 35:1996;2510-2512 Ito Y., Ogawa T.J. Am. Chem. Soc. 119:1997;5562-5566 Manabe S., Ito Y., Ogawa T. Synlett. 1998;628-630 Zhu T., Boons G.J. Tetrahedron: Asymmetry. 11:2000;199-205.
8. Ito Y., Kanie O., Ogawa T. Angew. Chem., Int. Ed. 35:1996;2510-2512 Ito Y., Ogawa T.J. Am. Chem. Soc. 119:1997;5562-5566 Manabe S., Ito Y., Ogawa T. Synlett. 1998;628-630 Zhu T., Boons G.J. Tetrahedron: Asymmetry. 11:2000;199-205.
9. Han H.S., Wolfe M.M., Brenner S., Janda K.D. Proc. Natl. Acad. Sci. U.S.A. 92:1995;6419-6423.
10. Douglas S.P., Whitfield D.M., Krepinsky J.J. J. Am. Chem. Soc. 117:1995;2116-2117.
11. Mehta S., Whitfield D. Tetrahedron Lett. 39:1998;5907-5910 Yan F.Y., Wakarchuk W.W., Gilbert M., Richards J.C., Whitfield D.M. Carbohydr. Res. 328:2000;3-16 Schmidt D., Thiem J. Chem. Commun. 2000;1919-1920.
12. Mehta S., Whitfield D. Tetrahedron Lett. 39:1998;5907-5910 Yan F.Y., Wakarchuk W.W., Gilbert M., Richards J.C., Whitfield D.M. Carbohydr. Res. 328:2000;3-16 Schmidt D., Thiem J. Chem. Commun. 2000;1919-1920.
13. Mehta S., Whitfield D. Tetrahedron Lett. 39:1998;5907-5910 Yan F.Y., Wakarchuk W.W., Gilbert M., Richards J.C., Whitfield D.M. Carbohydr. Res. 328:2000;3-16 Schmidt D., Thiem J. Chem. Commun. 2000;1919-1920.
14. Jesberger M., Jaunzems J., Jung A., Jas G., Schonberger A., Kirschning A. Synlett. 2000;1289-1293.
15. For linkers used in solid-phase oligosaccharide synthesis, see: Randolph J.T., McClure K.F., Danishefsky S.J. J. Am. Chem. Soc. 117:1995;5712-5719 Shimizu H., Ito Y., Kanie O., Ogawa T. Bioorg. Med. Chem. Lett. 6: 1996;2841-2846 Nicolaou K.C., Winssinger N., Pastor J., DeRoose F. J. Am. Chem. Soc. 119:1997;449-450 Doi T., Sugiki M., Yamada H., Takahashi T., Porco J.A. Tetrahedron Lett. 40:1999;2141-2144 Fukase K., Nakai Y., Egusa K., Porco J.A., Kusumoto S. Synlett. 1999;1074-1078 Andrade R.B., Plante O.J., Melean L.G., Seeberger P.H. Org. Lett. 1:1999;1811-1814.
16. For linkers used in solid-phase oligosaccharide synthesis, see: Randolph J.T., McClure K.F., Danishefsky S.J. J. Am. Chem. Soc. 117:1995;5712-5719 Shimizu H., Ito Y., Kanie O., Ogawa T. Bioorg. Med. Chem. Lett. 6: 1996;2841-2846 Nicolaou K.C., Winssinger N., Pastor J., DeRoose F. J. Am. Chem. Soc. 119:1997;449-450 Doi T., Sugiki M., Yamada H., Takahashi T., Porco J.A. Tetrahedron Lett. 40:1999;2141-2144 Fukase K., Nakai Y., Egusa K., Porco J.A., Kusumoto S. Synlett. 1999;1074-1078 Andrade R.B., Plante O.J., Melean L.G., Seeberger P.H. Org. Lett. 1:1999;1811-1814.
17. For linkers used in solid-phase oligosaccharide synthesis, see: Randolph J.T., McClure K.F., Danishefsky S.J. J. Am. Chem. Soc. 117:1995;5712-5719 Shimizu H., Ito Y., Kanie O., Ogawa T. Bioorg. Med. Chem. Lett. 6: 1996;2841-2846 Nicolaou K.C., Winssinger N., Pastor J., DeRoose F. J. Am. Chem. Soc. 119:1997;449-450 Doi T., Sugiki M., Yamada H., Takahashi T., Porco J.A. Tetrahedron Lett. 40:1999;2141-2144 Fukase K., Nakai Y., Egusa K., Porco J.A., Kusumoto S. Synlett. 1999;1074-1078 Andrade R.B., Plante O.J., Melean L.G., Seeberger P.H. Org. Lett. 1:1999;1811-1814.
18. For linkers used in solid-phase oligosaccharide synthesis, see: Randolph J.T., McClure K.F., Danishefsky S.J. J. Am. Chem. Soc. 117:1995;5712-5719 Shimizu H., Ito Y., Kanie O., Ogawa T. Bioorg. Med. Chem. Lett. 6: 1996;2841-2846 Nicolaou K.C., Winssinger N., Pastor J., DeRoose F. J. Am. Chem. Soc. 119:1997;449-450 Doi T., Sugiki M., Yamada H., Takahashi T., Porco J.A. Tetrahedron Lett. 40:1999;2141-2144 Fukase K., Nakai Y., Egusa K., Porco J.A., Kusumoto S. Synlett. 1999;1074-1078 Andrade R.B., Plante O.J., Melean L.G., Seeberger P.H. Org. Lett. 1:1999;1811-1814.
19. For linkers used in solid-phase oligosaccharide synthesis, see: Randolph J.T., McClure K.F., Danishefsky S.J. J. Am. Chem. Soc. 117:1995;5712-5719 Shimizu H., Ito Y., Kanie O., Ogawa T. Bioorg. Med. Chem. Lett. 6: 1996;2841-2846 Nicolaou K.C., Winssinger N., Pastor J., DeRoose F. J. Am. Chem. Soc. 119:1997;449-450 Doi T., Sugiki M., Yamada H., Takahashi T., Porco J.A. Tetrahedron Lett. 40:1999;2141-2144 Fukase K., Nakai Y., Egusa K., Porco J.A., Kusumoto S. Synlett. 1999;1074-1078 Andrade R.B., Plante O.J., Melean L.G., Seeberger P.H. Org. Lett. 1:1999;1811-1814.
20. For linkers used in solid-phase oligosaccharide synthesis, see: Randolph J.T., McClure K.F., Danishefsky S.J. J. Am. Chem. Soc. 117:1995;5712-5719 Shimizu H., Ito Y., Kanie O., Ogawa T. Bioorg. Med. Chem. Lett. 6: 1996;2841-2846 Nicolaou K.C., Winssinger N., Pastor J., DeRoose F. J. Am. Chem. Soc. 119:1997;449-450 Doi T., Sugiki M., Yamada H., Takahashi T., Porco J.A. Tetrahedron Lett. 40:1999;2141-2144 Fukase K., Nakai Y., Egusa K., Porco J.A., Kusumoto S. Synlett. 1999;1074-1078 Andrade R.B., Plante O.J., Melean L.G., Seeberger P.H. Org. Lett. 1:1999;1811-1814.
21. Matteucci M. Tetrahedron Lett. 31:1990;2385-2388 Jones R.J., Lin K.-Y., Milligan J.F., Wadwani S., Matteucci M.D. J. Org. Chem. 58:1993;2983-2991 Hashimoto H., Endo T., Kajihara Y. J. Org. Chem. 62:1997;1914-1915 Sawada D., Ito Y. Tetrahedron Lett. 42:2001;2501-2504.
22. Matteucci M. Tetrahedron Lett. 31:1990;2385-2388 Jones R.J., Lin K.-Y., Milligan J.F., Wadwani S., Matteucci M.D. J. Org. Chem. 58:1993;2983-2991 Hashimoto H., Endo T., Kajihara Y. J. Org. Chem. 62:1997;1914-1915 Sawada D., Ito Y. Tetrahedron Lett. 42:2001;2501-2504.
23. Matteucci M. Tetrahedron Lett. 31:1990;2385-2388 Jones R.J., Lin K.-Y., Milligan J.F., Wadwani S., Matteucci M.D. J. Org. Chem. 58:1993;2983-2991 Hashimoto H., Endo T., Kajihara Y. J. Org. Chem. 62:1997;1914-1915 Sawada D., Ito Y. Tetrahedron Lett. 42:2001;2501-2504.
24. Matteucci M. Tetrahedron Lett. 31:1990;2385-2388 Jones R.J., Lin K.-Y., Milligan J.F., Wadwani S., Matteucci M.D. J. Org. Chem. 58:1993;2983-2991 Hashimoto H., Endo T., Kajihara Y. J. Org. Chem. 62:1997;1914-1915 Sawada D., Ito Y. Tetrahedron Lett. 42:2001;2501-2504.
25. 1H NMR by using methoxy group ( δ 3.3) of MPEG as a standard, and recovery yield was based on its weight.
26. Pojer P.M., Angyal S.J. Aust. J. Chem. 31:1978;1031-1040.
27. The formation of unsymmetrical formylacetals for library construction is also under investigation by the reaction between MPEG-OH and various MTM ethers.
28. Cura P., Aloui M., Kartha K.P.R., Field R.A. Synlett. 2000;1279-1280.
29. The linker is stable even in the presence of higher amount (0.74 equiv) of TMSOTf at -40 °C.
30. Kim S., Park Y.H., Kee I.S. Tetrahedron Lett. 32:1991;3099-3100.
31. Herbert J.M., Knight J.G., Sexton B. Tetrahedron. 52:1996;15257-15266.
32. Corey E.J., Gras J.L., Ulrich P. Tetrahedron Lett. 1976;809-812.
33. Gross R.S., Watt D.S. Synth. Commun. 17:1987;1749-1760.
34. Rigby J.H., Wilson J.Z. Tetrahedron Lett. 25:1984;1429-1432.
35. Khalafi-Nezhad A., Alamdari R.F. Tetrahedron. 57:2001;6805-6807.
36. 1H NMR spectrum of the recovered MPEG revealed the cleavage of the disaccharide 13 had been completed. The spectrum also showed ca. 10% of MPEG had been clearly glycosylated with 9 , but this was not released from MPEG by trifluoroacetic acid.
37. Kozhevnikov I.V. Chem. Rev. 98:1998;171-198 Toshima K., Nagai H., Matsumura S. Synlett. 1999;1420-1422.
38. Kozhevnikov I.V. Chem. Rev. 98:1998;171-198 Toshima K., Nagai H., Matsumura S. Synlett. 1999;1420-1422.
39. We have also found that TentaGel OH resin, which has the PEG functionality as well, can be quantitatively functionalized by this protocol; Oikawa, M.; Sasaki, M., unpublished results.