New glycosylation reaction based on alkyne-Co2(CO)6 complex

Tetrahedron Letters

Volumn 38, Issue 26, 1997, Pages 4595-4598

  Mukai, Chisato ^a   Itoh, Takahiro ^a   Hanaoka, Miyoji ^a  

^a KANAZAWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

COBALT COMPLEX; GLYCOPYRANOSIDE;

ARTICLE; CHEMICAL MODIFICATION; COMPLEX FORMATION; GLYCOSYLATION; REACTION ANALYSIS;

EID: 0030902786     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00983-0     Document Type: Article

References (31)

1. Nicholas, K. M. Acc. Chem. Res. 1987, 20, 207 and references cited therein.
2. For example: (a) Fraser-Reid, B.; Konradsson, P.; Mootoo, D. R.; Udodong, U. J. Chem. Soc., Chem. Commun. 1988, 823.
3. (b) Rodebaugh, R.; Fraser-Reid, B. Tetrahedron 1996, 52, 7663.
4. For review: (a) Fraser-Reid, B.; Udodong, U. E.; Wu, Z.; Ottosson, H.; Merritt, J. R.; Rao, C. S.; Roberts, C.; Madsen, R. Synlett 1992, 927.
5. (b) Fraser-Reid, B. Acc. Chem. Res. 1996, 29, 57.
6. (a) Barresi, F.; Hindsgaul, O. J. Am. Chem. Soc. 1991, 113, 9376.
7. (b) Ito, Y.; Ogawa, T. Angew. Chem. Int. Ed. Engl. 1994, 33, 1765.
8. (c) Stork G.; Kim, G. J. Am. Chem. Soc. 1992, 114, 1087.
9. (d) Bols, M. J. Chem. Soc., Chem. Commun. 1992, 913.
10. (e) Krog-Jensen, C.; Oscarson, S. J. Org. Chem. 1996, 61, 4512.
11. (f) Iimori, T.; Shibazaki, T.; Ikegami, S. Tetrahedron Lett. 1996, 37, 2267.
12. 1H NMR spectroscopy.
13. 2, TMSOTf was found to be a suitable one for this reaction. In addition, it was shown that more than an equivalent of TMSOTf is necessary for consumption of the starting material.
14. For example: (a) Pougny, J.-R.; Jacquinet, J.-C.; Nassr, M.; Duchet, D.; Milat, M.-L.; Sinaÿ, P. J. Am. Chem. Soc. 1977, 99, 6762.
15. (b) Ito, Y.; Ogawa, T. Carbohydr. Res. 1990, 202, 165.
16. (c) Schmidt, R. R.; Gaden, H.; Jatzke, H. Tetrahedron Lett. 1990, 31, 327.
17. (d) Briner, K.; Vasella, A. Helv. Chim. Acta 1992, 75, 621.
18. Ratio of α to β was determined by HPLC.
19. When 11a (α : β = 28 : 72 or α : β = 99 : 1) was exposed to TMSOTf independently, 12a (α : β = 44 -45 : 56 - 54) was again obtained nonselectively regardless of composition of α and β isomers in the starting 11a. This observation strongly suggests that this reaction must proceed via the oxocarbenium cation species such as 3.
20. 2 = Bz
21. (a) Hashimoto, S.; Hayashi, M.; Noyori, R. Tetrahedron Lett. 1984, 25, 1379.
22. (b) Ratcliffe, A. J.; Fraser-Reid, B. J. Chem. Soc., Perkin Trans. 1 1990, 747.
23. (c) Schmidt, R. R.; Behrendt, M.; Toepfer, A. Synlett 1990, 694.
24. For example: Vankar, Y. D.; Vankar, P. S.; Behrebdt, M.; Schmidt, R. R. Tetrahedron 1991, 47, 9985.
25. For example: (a) Banoub, J.; Bundle, D. R. Can. J. Chem. 1979, 57, 2085.
26. (b) Suzuki, K.; Maeda, H.; Suzuki, T.; Matsumoto, T. Tetrahedron Lett. 1989, 30, 6879.
27. For example: (a) Hashimoto, S.; Honda, T.; Ikegami, S. J. Chem. Soc., Chem. Commun. 1989, 685.
28. (b) Marra, A.; Mallet, J. M.; amatore, C.; Sinaÿ, P. Synlett 1990, 572.
29. For example: Garegg, P. J.; Norberg, T. Acta Chem. Scan., Ser. B 1979, 33, 116.
30. (a) Kunz, H.; Harreus, A. Ann. Chem. 1982, 41.
31. (b) Garegg, P. J.; Konradsson, P.; Kvarnström, I.; Norberg, T.; Svensson, S. C. T.; Wigilius, B. Acta Chem. Scan., Ser. B 1985, 39, 569.