Abstract
A new method was developed for trimethylsilylation of alcohols by the reactions with (trifluoromethyl)trimethylsilane in the presence of tetrabutylammonium fluoride. The reactions of ecdysteroids (20-hydroxyecdysone, its 20,22-mono- and 2,3:20,22-diacetonides, and polypodine B) and carbohydrates (D-gluco-, D-galacto-, and D-xylopyranoses) afforded the corresponding persilylated derivatives.
Similar content being viewed by others
References
M. Lalonde and T. H. Chan, Synthesis, 1985, 817.
G. A. Olah, B. G. B. Gupta, and S. C. Narang, J. Org. Chem., 1979, 44, 4272.
U. Hedtmann, R. Kliniz, K. Hobert, J. Frelek, I. Vlanov, and P. Welzel, Tetrahedron, 1991, 47, 3753.
V. N. Odinokov, R. G. Savchenko, S. R. Nazmeeva, and I. V. Galyautdinov, Izv. Akad. Nauk, Ser. Khim., 2002, 1810 [Russ. Chem. Bull., Int. Ed., 2002, 51, 1963].
E. Breitmaier and W. Voelter, 13C NMR Spectroscopy, Verlag Chemie, Weinheim, 1974, 276 p.
S. G. K. Prakash and A. K. Yudin, Chem. Rev., 1997, 97, 757.
R. P. Singh and J. M. Shreeve, Tetrahedron, 2000, 56, 7613.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Odinokov, V.N., Savchenko, R.G., Nazmeeva, S.R. et al. New method for trimethylsilylation of hydroxy-containing compounds. Synthesis of persilylated ecdysteroids and carbohydrates. Russian Chemical Bulletin 51, 1937–1939 (2002). https://doi.org/10.1023/A:1021377207689
Issue Date:
DOI: https://doi.org/10.1023/A:1021377207689