Electronic factors in the C-glycosidation with silylacetylene

Chemistry Letters

Volumn , Issue 6, 1999, Pages 467-468

  Isobe, Minoru ^a   Saeeng, Rungnapha ^a   Nishizawa, Rena ^a   Konobe, Masato ^a   Nishikawa, Toshio ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0033241948     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1999.467     Document Type: Article

References (12)

1. a) Y. Ichikawa, M. Isobe, M, Konobe, and T. Goto, Carbohydr. Res., 171, 193 (1987).
2. b) M. Isobe, R. Nishizawa, S. Hosokawa, and T. Nishikawa, J. Chem. Soc., Chem. Commun., 1998, 2665.
3. a) S. Hosokawa and M. Isobe, J. Org. Chem., 64, 37 (1999), and references cited therein,
4. b) R. Saeeng and M. Isobe, Tetrahedron Lett., 40, 1911 (1999).
5. An intermediate 4a in eq. 2 is reported in the following paper. T. Tsukiyama and M. Isobe, Tetrahedron Lett., 33, 7911 (1992).
6. T. Tsukiyama, S. C. Peters, and M. Isobe, Synlett, 1993, 413.
7. 6Si; C, 68.75 ; H, 6.76%.
8. 5Si; C, 69.80; H, 6.94%.
9. a) S. Hosokawa, B. Kirschbaum, and M. Isobe, Tetrahedron Lett., 39, 1917 (1998).
10. b) S. Hosokawa and M. Isobe, Synlett, 1996, 351.
11. M. Miljkovic, D. Yeagley, P. Deslongchamps, and Y. L. Dory, J. Org. Chem., 62, 7597 (1997).
12. a) The yield of product from C-glycosidation of Bistrimelhylsilylacetylene with 7 (R= Ac) and (R= Me) were 85 and 56% and the yield with 8 (R= Ac) and (R= Me) were 68 and 60%, respectively, b) The mixing reaction as eq. 4 and eq. 5 were conducted with only 1 equiv. of the reagent and interrupted while starting materials were remained, so that the products were kinetically controlled and the yields being 10-60%.