Unique reactivity of the Mukaiyama glycosidation catalyst (SnCl 3ClO4) toward β-mannopyranosides

Chemistry - An Asian Journal

Volumn 3, Issue 2, 2008, Pages 319-326

  Wang, Yonghui ^a   Cheon, Hwan Sung ^a   Kishi, Yoshito ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

Anomeric effect; Anomerization; Delta2 effect; Glycosidation; Glycosides

Indexed keywords

MANNOSE; PERCHLORIC ACID; TIN DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; GLYCOSYLATION;

CATALYSIS; GLYCOSYLATION; MANNOSE; MOLECULAR STRUCTURE; PERCHLORIC ACID; TIN COMPOUNDS;

EID: 40149083156     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.200700297     Document Type: Article

References (49)

1. For a review on this subject, see: K. Bloch, Adv. Enzymol. 1977, 45, 1.
2. Isolation and characterization of nMMPs: a) G. R. Gary, G. C. E. Ballou, J. Biol. Chem. 1971, 246, 6835;
3. b) M. Ilton, A. W. Jevans, E. D. McCarthy, D. Vance, H. B. White III, K. Bloch, Proc. Natl. Acad. Sci. USA 1971, 68, 87;
4. c) S. K. Maitra, C. E. Ballou, J. Biol. Chem. 1977, 252, 2459;
5. isolation and characterization of nMGLPs: d) Y. C. Lee, C. E. Ballou, J. Biol. Chem. 1964, 239, PC3602;
6. e) L. S. Forsberg, A. Dell, D. J. Walton, C. E. Ballou, J. Biol. Chem. 1982, 257, 3555;
7. revised structure of nMGLP: f) G. Tuffal, R. Albigot, M. Rivière, G. Puzo, Glycobiology 1998, 8, 675.
8. a) M. C. Hsu, J. Lee, Y. Kishi, J. Org. Chem. 2007, 72, 1931;
9. b) M. Meppen, Y. Wang, H.-S. Cheon, Y. Kishi, J. Org. Chem. 2007, 72, 1941;
10. c) Y. Wang, J. Ma, H.-S. Cheon, Y. Kishi, Angew. Chem. 2007, 119, 1355;
11. Angew. Chem. Int. Ed. 2007, 46, 1333;
12. d) J. Ma, H.-S. Cheon, Y. Kishi, Org. Lett. 2007, 9, 319;
13. e) H.-S. Cheon, Y. Wang, J. Ma, Y. Kishi, ChemBioChem 2007, 8, 353;
14. f) H. S. Cheon, Y. Lian, Y. Kishi, Org. Lett. 2007, 9, 3323;
15. g) H.-S. Cheon, Y. Lian, Y. Kishi, Org. Lett. 2007, 9, 3327;
16. h) N. Papaioannou, H.-S. Cheon, Y. Lian, Y. Kishi, ChemBioChem 2007, 8, 1775.
17. a) T. Mukaiyama, T. Takashima, M. Katurada, H. Aizawa, Chem. Lett. 1991, 533;
18. b) T. Mukaiyam, M. Katsurada, T. Takashima, Chem. Lett. 1991, 985;
19. c) K. Matsubara, T. Sasaki, T. Mukaiyama, Chem. Lett. 1993, 1373;
20. d) K. Matsubara, T. Mukaiyama, Chem. Lett. 1994, 247;
21. e) T. Iimori, I. Azumaya, T. Shibazaki, S. Ikegami, Heterocycles 1997, 46, 221, and references therein.
22. a) R. U. Lemieux, Adv. Carbohydr. Chem. 1954, 9, 1;
23. b) R. U. Lemieux in Molecular Rearrangements (Ed.: P. De Mayo), Interscience, New York, 1964, pp. 709-769.
24. For a recent review on this subject, see: S. Koto in Glycoscience: Chemistry and Chemical Biology (Eds.: B. O. Fraser-Reid, K. Tatsuta, J. Thiem), Springer, Berlin, 2002, pp. 785-874.
25. [3a] the experimental observations made suggested that the β-to-α anomerization is virtually kinetically controlled for the reaction within 10 h. However, with longer reaction times, the scrambled products were observed at least in the octasaccharide series, thereby implying that formation of oxonium ion(s) from the a anomer is feasible, although very sluggish.
26. [6]
27. 4: K. Masubara, T. Mukaiyama, Chem. Lett. 1993, 2145: to our knowledge, however, no anomerization of a 2-oxypyranoside was reported under the Mukaiyama conditions.
28. 2O.
29. Among numerous examples known in literature, the example reported by Lee and co-workers is most relevant to the current case: C. K. Lee, E. J. Kim, I.-S. H. Lee, Carbohydr. Res. 1993, 240, 197.
30. For a detailed analysis on the endocyclic and exocyclic cleavage of pyranoside acetals, see, for example: a) reference [14a];
31. b) J. L. Liras, V. M. Lynch, E. V. Anslyn, J. Am. Chem. Soc. 1997, 119, 8191.
32. 4: N. Morishima, S. Koto, S. Zen, Chem. Lett. 1979, 749;
33. S. Koto, N. Morishima, R. Kawahara, K. Ishikawa, S. Zen, Bull. Chem. Soc. Jpn. 1982, 55, 1092;
34. 4: T. Mukaiyama, K. Takeuchi, H. Uchiro, H. Chem. Lett. 1997, 625;
35. 3: N. Ikemoto, O. K. Kim, L.-C. Chiang, V. Satyanarayana, M. Chang, K. Nakanishi, Tetrahedron Lett. 1992, 33, 4295;
36. 2BBr: Y. Guindon, P. C. Anderson, Tetrahedron Lett. 1987, 28, 2485;
37. Y. Guindon, P. C. Anderson, C. Yoakim, Y. Girard, Pure. Appl. Chem. 1988, 60, 1705;
38. 3: R. Olsson, U. Berg, Tetrahedron 1998, 54, 3935;
39. TMSOTf: K. C. Lee, E. L. Kim, I.-S. H. Lee, Carbohydr. Res. 1993, 240, 197;
40. C. K. Lee, E. L. Kim, I.-S. H. Lee, Carbohydr. Res. 1998, 309, 243.
41. For monographs on this subject, see: a) P. Deslongchamps, Stereoelectronic Effects in Organic Chemistry, Pergamon, Oxford, 1983;
42. b) A. J. Kirby, The Anomeric Effect and Related Stereoelectronic Effects at Oxygen, Springer, Berlin, 1983.
43. R. E. Reeves, J. Am. Chem. Soc. 1950, 72, 1499.
44. For a review on this subject, see: V. S. R. Rao, P. K. Qasba, P. V. Balaji, R. Chandrasekaran, Conformation of Carbohydrates, Harwood, Amsterdam, 1998, chap. 3, pp. 49- 90.
45. Extrapolating the subgroup analysis in Scheme 7, we noticed the possibility that the Mukaiyama glycosidation catalyst might be developed as a selective cleavage reagent of a β-glycosidic linkage present in a permethylated polysaccharide.
46. a) S. S. Bhattacharjee, P. A. Gorin, Can. J. Chem. 1969, 47, 1195;
47. b) A. Lipták, I. Jodál, P. Nánási, Carbohydr. Res. 1975, 44, 1.
48. a) S. David, A. Thieffry, A. Veyrières, J. Chem. Soc. Perkin Trans. 1 1981, 1796;
49. b) W. R. Roush, M. R. Michaelides, D. F. Tai, B. M. Lesur, W. K. M. Chong, D. J. Harris, J. Am. Chem. Soc. 1989, 111, 2984.