References
- Harmon , R. E. , Robbins , R. K. and Townsend , L. B. , eds. 1978 . “ Chemistry and Biology of Nucleosides and Nucleotides ” . New York : Academic Press, Inc. .
- Johnson , T. B. and Hilbert , G. E. 1929 . Science , 69 : 579 Johnson, T. B., Hilbert, G. E., J. Amer. Chem. Soc. 52, (1930)., 2001.
- Wittenburg , E. 1964 . Z. Chem. , 4 : 303 Wittenburg, E., Chem. Ber. 1968, 101, 1095.
- Niedballa , U. and Vorbruggen , H. 1974 . J. Org. Chem. , 39 : 3654 (b) Ibid 1974, 39, 3660. (c) Ibid 1974, 39, 3664. (d) Ibid 1974, 39, 3668. (e) Ibid 1974, 39, 3672. (f) Ibid 1976, 41, 2084. (g) Hofle, G., Vorbruggen, H., Chem. Ber 1981, 114, 1256. (h) Vorbruggen, H., Niedballa, U., U. S. Patent 3,748,320, 1973.
- Skulnick , H. 1978 . J. Org. Chem. , 43 : 3188 For reports of good selectivity using SnCl4 in mixed solvent systems see
- Hubbard , A. J. , Jones , A. S. and Walker , R. T. 1984 . Nucleic Acid Res. , 12 : 6827
- Hoffer , M. 1960 . Chem. Ber. , 93 : 2771
- Kotick , M. P. , Szantay , C. and Bardos , T. J. 1969 . J. Org. Chem. , 34 : 3806 Solvents of high dielectric constant promote anomerization of the chlorosugar and it has been noted (Ref. 6) that the β-chlorosugar reacts faster to produce α-nucleoside then α-chlorosugar gives β-nucleoside. See also
- This implies that CuI is not acting as a Friedel Crafts catalyst as Vorbruggen has shown4g that electron withdrawing substituents in the 5 position give faster reactions. .
- Walker , R. T. Private Communication with Prof
- ZnCl2 also yields predominantly β-product in high yield (Ref 6). .
- Burkhalter , J. H. and Scarborough , H. C. 1955 . J. Amer. Pharm. Asso. , 44 : 545
- Hoffer , M. , Duschinsky , R. , Fox , J. J. and Yung , N. 1959 . J. Amer. Chem. Soc. , 81 : 4112
- Pliml , J. , Prystas , M. and Sorm , F. 1963 . Coll. Czech Chem. Commun. , 28 : 2588