A catalytic one-step process for the chemo- and regioselective acylation of monosaccharides

Journal of the American Chemical Society

Volumn 129, Issue 42, 2007, Pages 12890-12895

  Kawabata, Takeo ^a   Muramatsu, Wataru ^a   Nishio, Tadashi ^a   Shibata, Takeshi ^a   Schedel, Hartmut ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROXYL GROUPS; MONOSACCHARIDES; REGIOSELECTIVE ACYLATION;

ACYLATION; CATALYST ACTIVITY; HYDROGEN BONDS; REGIOSELECTIVITY;

SUGAR (SUCROSE);

4 PYRROLIDINOPYRIDINE; ACID ANHYDRIDE; GLUCOPYRANOSIDE; ISOBUTYRIC ACID; MONOSACCHARIDE; OCTYL BETA GLUCOSIDE; PHENETHYL ALCOHOL; PYRIDINE DERIVATIVE; PYRROLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; CARBOHYDRATE ANALYSIS; CARBOHYDRATE SYNTHESIS; CATALYSIS; HYDROGEN BOND; STEREOCHEMISTRY; STEREOSPECIFICITY;

CARBOHYDRATE CONFORMATION; CARBOHYDRATES; CATALYSIS; CHEMISTRY, ORGANIC; HYDROGEN BONDING; HYDROLYSIS; MODELS, CHEMICAL; MOLECULAR STRUCTURE; MONOSACCHARIDES; PYRANS; SOLVENTS; STEREOISOMERISM;

EID: 35549002267     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja074882e     Document Type: Article

References (40)

1. Doores, K. J.; Gamblin, D. P.; Davis, B. G. Chem. - Eur. J. 2006, 12, 656.
2. Bartolozzi, A.; Seeberger, P. H. Curr. Opin. Struct. Biol. 2001, 11, 587.
3. Therisod, M.; Klibanov, A. M. J. Am. Chem. Soc. 1987, 109, 3977.
4. Björkling, F.; Godtfredsen, S. E.; Kirk, O. J. Chem. Soc., Chem. Commun. 1989, 934.
5. Kattnig, E.; Albert, M. Org. Lett. 2004, 6, 945.
6. (a) Kurahashi, T.; Mizutani, T.; Yoshida, J. J. Chem. Soc., Perkin Trans. 1 1999, 465.
7. (b) Kurahashi, T.; Mizutani, Tadashi.; Yoshida, J. Tetrahedron 2002, 58, 8669.
8. Griswold, K. S.; Miller, S. J. Tetrahedron 2003, 59, 8869.
9. Site-selective acylation of erythromycin has recently been developed. See: Lewis, C. A.; Miller, S. J. Angew. Chem., Int. Ed. 2006, 45, 5616.
10. We recently reported regioselective acylation of 6-O-protected octyl β-D-glucopyranosides by DMAP catalysis. See: Muramatsu, W.; Kawabata, T. Tetrahedron Lett. 2007, 48, 5031.
11. Scriven, E. F. V. Chem. Soc. Rev. 1983, 12, 129.
12. Höfle, G.; Steglich, W.; Vorbrüggen, H. Angew. Chem., Int. Ed. Engl. 1978, 17, 569.
13. Vacca, A.; Nativi, C.; Cacciarini, M.; Pergoli, R.; Roelens, S. J. Am. Chem. Soc. 2004, 126, 16456.
14. Verdoucq, L.; Moriniére, J.; Bevan, D. R.; Esen, A.; Vasella, A.; Henrissat, B.; Czjzek, M. J. Biol. Chem. 2004, 279, 31796.
15. Chiral PPY and DMAP analogues have been developed for enantioselective catalysis. See: (a) Vedejs, E.; Chen, X. J. Am. Chem. Soc. 1996, 118, 1809.
16. (b) Ruble, J. C.; Fu, G. C. J. Org. Chem. 1996, 61, 7230.
17. (c) Ruble, J. C.; Latham, H. A.; Fu, G. C. J. Am. Chem. Soc. 1997, 119, 1492.
18. (d) Kawabata, T.; Nagato, M.; Takasu, K.; Fuji, K. J. Am. Chem. Soc. 1997, 119, 3169.
19. (e) Ruble, J. C.; Fu, G. C. J. Am. Chem. Soc. 1998, 120, 11532.
20. (f) Liang, J.; Ruble, J. C.; Fu, G. C. J. Org. Chem. 1998, 63, 3154.
21. (g) Hodous, B. L.; Ruble, J. C.; Fu, G. C. J. Am. Chem. Soc. 1999, 121, 2637.
22. (h) Ie, Y.; Fu, G. C. Chem. Commun. 2000, 119.
23. (i) Spivey, A. C.; Fekner, T.; Spey, S. E. J. Org. Chem. 2000, 65, 3154.
24. (j) Spivey, A. C.; Maddaford, A.; Fekner, T.; Redgrave, A. J.; Frampton, C. S. J. Chem. Soc., Perkin Trans. 1 2000, 3460.
25. (k) Arai, S.; Bellemin-Laponnaz, S.; Fu, G. C. Angew. Chem., Int. Ed. 2001, 40, 647.
26. (l) Priem, G.; Anson, M. S.; Macdonald, S. J. F.; Pelotier, B.; Campbell, I. B. Tetrahedron Lett. 2002, 43, 6001.
27. (m) Kim, K.-S.; Park, S.-H.; Chang, H.-J.; Kim, K. S. Chem. Lett. 2002, 1114.
28. (n) Shaw, S. A.; Aleman, P.; Vedejs, E. J. Am. Chem. Soc. 2003, 125, 13368.
29. (o) Spivey, A. C.; Zhu. F.; Mitchell, M. B.; Davey, S. G.; Jarvest, R. L. J. Org. Chem. 2003, 68, 7379.
30. (p) Tabanella, S.; Valanocogne, I.; Jackson, R. F. W. Org. Biomol. Chem. 2003, 1, 4254.
31. (q) Priem, G.; Pelotier, B.; Macdonald, S. J. F.; Anson, M. S.; Campbell, I. B. J. Org. Chem. 2003, 68, 3844.
32. (r) Pelotier, B.; Priem, G.; Campbell, I. B.; Macdonald, S. J. F.; Anson, M. S. Synlett 2003, 679.
33. (s) Kawabata, T.; Stragies, R.; Fukaya, T.; Fuji, K. Chirality 2003, 15, 71.
34. (t) Kawabata, T.; Stragies, R.; Fukuya, T.; Nagaoka, Y.; Schedel, H.; Fuji, K. Tetrahedron Lett. 2003, 44, 1545.
35. (u) Spivey, A. C.; Leese, D. P.; Zhu, F.; Davey, S. G.; Jarvest, R. L. Tetrahedron 2004, 60, 4513.
36. (v) Arp, F. O.; Fu, G. C. J. Am. Chem. Soc. 2006, 128, 14264.
37. Kawabata, T.; Yamamoto, K.; Momose, Y.; Nagaoka, Y.; Yoshida, H.; Fuji, K. Chem. Commun. 2001, 2700.
38. Fischer, C. B.; Xu, S.; Zipse, H. Chem. - Eur. J. 2006, 12, 5779.
39. 2 column chromatography (ethyl acetate/hexane = 30:70 to 100:0) to give a 99:1 mixture of octyl 4-O-isobutyryl-β-D-glucopyranoside and octyl 3-O-isobutyryl-β-D-glucopyranoside in a combined yield of 98% (71 mg). Identification of the regioisomeric products was unambiguously performed by the comparison with pure regioisomers prepared independently by a conventional protection/deprotection procedure (see Supporting Information).
40. Nicolaou, K. C.; Seitz, S. P.; Papahatjis, D. P. J. Am. Chem. Soc. 1983, 105, 2430.