Rapid glycosylations under extremely mild acidic conditions. Use of ammonium salts to activate glycosyl phosphites via P-protonation

Carbohydrate Research

Volumn 345, Issue 9, 2010, Pages 1211-1215

  Matsumura, Fumiko ^a   Tatsumi, Shiro ^a   Oka, Natsuhisa ^a   Wada, Takeshi ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

4,4 Dimethoxytrityl group; Ammonium salts; Glycosyl phosphites; Glycosylation; P Protonation

Indexed keywords

ACID-LABILE; ACIDIC ACTIVATORS; AMMONIUM SALT; AMMONIUM SALTS; GLYCOSYL; GLYCOSYL DONORS; GLYCOSYL PHOSPHITES; GLYCOSYLATIONS; GOOD YIELD; MILD ACIDIC CONDITIONS; TERTIARY AMINE; TRANSIENT PROTECTION; TRIESTERS; TRIFLUOROMETHANE SULFONIC ACID;

ACIDS; AMMONIUM COMPOUNDS; ESTERIFICATION; GLYCOSYLATION; PROTONATION;

SALTS;

AMMONIA; DISACCHARIDE; MONOSACCHARIDE; PHOSPHITE; TRIFLUOROMETHANESULFONIC ACID; TRISTEARIN; INORGANIC SALT; PHOSPHORUS; PROTON; QUATERNARY AMMONIUM DERIVATIVE;

ACIDITY; ARTICLE; CONTROLLED STUDY; GLYCOSYLATION; PRIORITY JOURNAL; PROTON TRANSPORT; CHEMISTRY; KINETICS; PH;

GLYCOSYLATION; HYDROGEN-ION CONCENTRATION; KINETICS; PHOSPHITES; PHOSPHORUS; PROTONS; QUATERNARY AMMONIUM COMPOUNDS; SALTS;

EID: 77953140340     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carres.2010.03.009     Document Type: Article

References (43)

1. Varki A. Glycobiology 3 (1993) 97-130
2. Lis H., and Sharon N. Eur. J. Biochem. 218 (1993) 1-27
3. Kolter T., and Sandhoff K. Angew. Chem., Int. Ed. 38 (1999) 1532-1568
4. Sears P., and Wong C.-H. Science 291 (2001) 2344-2350
5. Bertozzi C.R., and Kiessling L.L. Science 291 (2001) 2357-2364
6. Seeberger P.H. Carbohydr. Res. 343 (2008) 1889-1896
7. Aich U., and Yarema K.J. In: Fraser-Reid B., Tatsuta K., and Thiem J. (Eds). Glycoscience. 2nd ed. Vol. 3 (2008), Springer, Berlin, Heidelberg, New York 2133-2190
8. Seeberger P.H., and Werz D.B. Nat. Rev. Drug Disc. 4 (2005) 751-763
9. Seeberger P.H., and Werz D.B. Nature 446 (2007) 1046-1051
10. Kondo H., Ichikawa Y., and Wong C.-H. J. Am. Chem. Soc. 114 (1992) 8748-8750
11. Martin T.J., and Schmidt R.R. Tetrahedron Lett. 33 (1992) 6123-6126
12. Watanabe Y., Nakamoto C., and Ozaki S. Synlett (1993) 115-116
13. Kondo H., Aoki S., Ichikawa Y., Halcomb R.L., Ritzen H., and Wong C.-H. J. Org. Chem. 59 (1994) 864-877
14. Watanabe Y., Nakamoto C., Yamamoto T., and Ozaki S. Tetrahedron 50 (1994) 6523-6536
15. Hashimoto S., Umeo K., Sano A., Watanabe N., Nakajima M., and Ikegami S. Tetrahedron Lett. 36 (1995) 2251-2254
16. Tanaka H., Sakamoto H., Sano A., Nakamura S., Nakajima M., and Hashimoto S. Chem. Commun. (1999) 1259-1260
17. Nagai H., Matsumura S., and Toshima K. Tetrahedron Lett. 43 (2002) 847-850
18. Nagai H., Matsumura S., and Toshima K. Carbohydr. Res. 338 (2003) 1531-1534
19. Nagai H., Sasaki K., Matsumura S., and Toshima K. Carbohydr. Res. 340 (2005) 337-353
20. Arihara R., Nakamura S., and Hashimoto S. Angew. Chem., Int. Ed. 44 (2005) 2245-2249
21. Adinolfi M., Iadonisi A., and Schiattarella M. Tetrahedron Lett. 44 (2003) 6479-6482
22. El-Badri M.H., Willenbring D., Tantillo D.J., and Gervay-Hague J. J. Org. Chem. 72 (2007) 4663-4672
23. Smith M., Rammler D.H., Goldberg I.H., and Khorana H.G. J. Am. Chem. Soc. 84 (1962) 430-440
24. Beaucage S.L., and Iyer R.P. Tetrahedron 48 (1992) 2223-2311
25. Valerio S., Iadonisi A., Adinolfi M., and Ravidà A. J. Org. Chem. 72 (2007) 6097-6106
26. Fei C.P., and Chan T.H. Tetrahedron Lett. 28 (1987) 849-852
27. Houdier S., and Vottero P.J.A. Carbohydr. Res. 232 (1992) 349-352
28. Fukase K., Nakai Y., Kanoh T., and Kusumoto S. Synlett (1998) 84-86
29. Gramstad T., and Haszeldine R.N. J. Chem. Soc. (1957) 4069-4079
30. Oka N., Wada T., and Saigo K. J. Am. Chem. Soc. 125 (2003) 8307-8317
31. Leroux J., and Perlin A.S. Carbohydr. Res. 67 (1978) 163-178
32. Oka N., Wada T., and Saigo K. J. Am. Chem. Soc. 124 (2002) 4962-4963
33. Wada T., Maizuru Y., Shimizu M., Oka N., and Saigo K. Bioorg. Med. Chem. Lett. 16 (2006) 3111-3114
34. Oka N., Yamamoto M., Sato T., and Wada T. J. Am. Chem. Soc. 130 (2008) 16031-16037
35. Iwamoto N., Oka N., Sato T., and Wada T. Angew. Chem., Int. Ed. 48 (2009) 496-499
36. Oka N., Kondo T., Fujiwara S., Maizuru Y., and Wada T. Org. Lett. 11 (2009) 967-970
37. Crich D., and Sun S. Tetrahedron 54 (1998) 8321-8348
38. Callam C.S., Gadikota R.R., Krein D.M., and Lowary T.L. J. Am. Chem. Soc. 125 (2003) 13112-13119
39. See Supplementary data.
40. Shimizu M., Wada T., Oka N., and Saigo K. J. Org. Chem. 69 (2004) 5261-5268
41. Kovác P., Sklenár V., and Glaudemans C.P.J. Carbohydr. Res. 175 (1988) 201-213
42. Schmidt R.R., Moering U., and Reichrath M. Chem. Ber. 115 (1982) 39-49
43. Pearce A.J., Sollogoub M., Mallet J.-M., and Sinaÿ P. Eur. J. Org. Chem. (1999) 2103-2117