Abstract
The title compound (II) was prepared by treating dry, purified α-cyclodextrin with 20 equivalents oft-butyldimethylsilyl chloride 20 hr at 110° in DMF/pyridine. Work-up of the product mixture gave 60%II, which was identified by1H and13C NMR. Treatment ofII with Bu4NF 6 hr in refluxing dry THF efficiently removed the protecting groups.
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Notes and References
M. L. Bender and M. Komiyama:Cyclodextrin Chemistry, Springer-Verlag (1978);
J. Szejtli:Cyclodextrins and Their Complexes, Akademiai Kiado (1982);
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We have observed that pyridine as a catalyst gives a higher yield ofII than does the more-frequently used imidazole.
IR: (vOH (stretch), 3440 cm−1,vSi-(CH3)3 1250 cm−1), m.p. 274°C (decomposition),1H,13C NMR: JEOL, JNM-FX270, multinuclear, CDCl3-TMS. Elemental analysis: calculated for formula: C108H228O30Si12, C-55.34, H-9.81, O-20.48, Si-14.38. Found: C-55.39, H-9.97, O-19.35, Si-14.56.
Assignments for most of the signals in the13C NMR spectra were based upon data on cyclodextrins and other carbohydrates, e.g., P. Colson, H. J. Jennings, and J. C. P. Smith:J. Am. Chem. Soc. 96, 8081 (1974); K. Takeo, K. Hirose, and T. Kluge:Chem. Lett. 1233 (1973); J. Boger, R. Corcoran, and J.-M. Lehn:Helv. Chim. Acta 61, 2190 (1978).
13C NMR Spectroscopy, Verlag-Chemie pp. 223–242, 1975. See also J. Bogeret al. [2] and R. L. Wifeet al. [3].
E. J. Corey and L. Vankateswarlu:J. Am. Chem. Soc. 94, 6190 (1972).
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Michalski, T.J., Kendler, A. & Bender, M.L. A silyl-α-cyclodextrin intermediate. Preparation and characterization of dodeca-t-butyldimethylsilyl-hexahydroxy-α-cyclodextrin. Journal of Inclusion Phenomena 1, 125–128 (1983). https://doi.org/10.1007/BF00656814
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DOI: https://doi.org/10.1007/BF00656814