Bismuth(III) triflate-catalyzed dehydrative glycosidation using 1-hydroxy sugars

Letters in Organic Chemistry

Volumn 5, Issue 1, 2008, Pages 30-33

  Yamanoi, Takashi ^a   Inoue, Ryo ^a,b   Matsuda, Sho ^a   Hamasaki, Keita ^b  

^a NOGUCHI INSTITUTE   (Japan)

^b SHIBAURA INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

1,1' disaccharide; 1 hydroxy sugar; Bismuth(III) triflate; Glycosidation; Glycoside

Indexed keywords

EID: 38949216070     PISSN: 15701786     EISSN: None     Source Type: Journal    
DOI: 10.2174/157017808783330289     Document Type: Article

References (19)

1. a) Toshima, K.; Tatuta, K. Chem. Rev., 1993, 93, 1503;
2. b) Panza, L.; Lay, L. In Carbohydrates in Chemistry and Biology; Ernst, B.; Hart G. W.; Sinay, P. Eds.; Wiley-VCH: Weinheim, 2000; Vol. 1, pp. 195-237;
3. c) Demchenko, A. V. Synlett, 2003, 1225;
4. d) Aoyama, N.; Kobayashi, S. Chem. Lett., 2006, 35, 238-239. Recent references cited therein.
5. Mukaiyama, T.; Matsubara, K.; Hora, M. Synthesis, 1994, 1368.
6. a) Yamanoi, T.; Inoue, R.; Matsuda, S.; Katsuraya, K.; Hamasaki, K. Tetrahedron: Asymnetry, 2006, 17, 2914;
7. b) Yamanoi, T.; Oda, Y.; Matsuda, S.; Yamazaki, I.; Matsumura, K.; Katsuraya, K.; Watanabe, M.; Inazu, T. Tetrahedron, 2006, 62, 10383;
8. c) Yamanoi, T.; Matsuda, S.; Yamazaki, I.; Inoue, R.; Hamasaki, K.; Watanabe, M. Heterocycles, 2006, 68, 673;
9. d) Yamanoi, T.; Matsumura, K.; Matsuda, S.; Oda, Y. Synlett, 2005, 2973.
10. 3 Adinolfi, M.; Iadonisi, A.; Ravida, A.; Valerio, S. Tetrahedron Lett., 2006, 47, 2595;
11. b) Ikeda, K.; Torisawa, Y.; Nishi, T.; Minamikawa, J.; Tanaka, K.; Sato, M. Bioorg. Med. Chem., 2003, 11, 3073.
12. Anhydrous calcium sulfate was used as a scavenger for water. We have already investigated the glycosidation catalyzed by a Lewis acid in the presence of several anhydrous salts. Yamanoi, T.; Nagamaya, S.; Ishida, H.-K.; Nishikido, J.; Inazu, T. Synth. Commun., 2001, 31, 899.
13. 4, the solvent was evaporated under reduced pressure. The crude product was purified by preparative silica gel TLC (ethyl acetate/hexane=1/3) to give the desired glycoside 10 (92.4 mg, 87%) as a colorless oil and the 1,1′-disaccharide 19 (α, β-mixture, 8.3 mg, 9%) as a colorless oil. All the other glycosides 11-18 were similarly prepared and purified by preparative silica gel TLC (11, 12, 14-18: ethyl acetate/hexane = 1/3; 13: toluene/ethyl acetate = 10/1). The spectral data of 11-14, 16, 19-21 are reported in the literatures.
14. See, 11: Nagai, H.; Sasaki, K.; Matsumura, S.; Toshima, K. Carbohydr. Res., 2005, 340, 337;
15. 12 and 13: Garcia, B. A.; Gin, D. Y. J. Am. Chem. Soc., 2000, 122, 4269;
16. 14: Crich, D.; Sun, S. Tetrahedron, 1998, 54, 8321;
17. 16: Toshima, K.; Nagai, H.; Kusumi, K.; Kawahara, K.; Matsumura, S. Tetrahedron, 2004, 60, 5331;
18. 19, 20 and 21: Pavia, A. A.; Rocheville, J.-M.; Ung, S. N. Carbohydr. Res., 1980, 79,79.
19. 2Phβ), 73.1 (α), 73.36 (β), 73.41 (α), 74.6 (β), 74.80 (β), 74.82 (α), 74.9 (β), 75.59 (β), 75.60 (α), 77.6 (α), 77.8 (β), 80.0 (C-2α), 81.9 (α), 82.2 (β), 84.6 (β), 96.8 (C-1α), 103.6 (C-1β)