A divergent approach toward synthesis of myoinositol phosphates: Acyl migrations and regioselectivity

Pure and Applied Chemistry

Volumn 68, Issue 4, 1996, Pages 931-935

  Chung, Sung Kee ^a   Chang, Young Tae ^a   Ryu, Youngha ^a  

^a Pohang University of Science and Technology (POSTECH)   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0038499152     PISSN: 00334545     EISSN: None     Source Type: Journal    
DOI: 10.1351/pac199668040931     Document Type: Article

References (18)

1. M. J. Berridge, Nature (London), 1993, 361, 315.
2. R. F. Irvine and P. J. Cullen, Current Biology, 1993, 3, 540.
3. S. B. Shears, Biochem. J., 1989, 260, 313.
4. S. K. Chung and Y. T. Chang, J. Chem. Soc. Chem. Commun., 1995, 11.
5. S. K. Chung, Y. T. Chang and K. H. Sohn, submitted for publication.
6. F. D. Gunstone, "Compre. Org. Chem.", Pergamon Press, London, 1979, vol. 6, p 633.
7. R. M. Rowell, Carbohydr. Res., 1972, 23, 417.
8. S. M. Hecht, Acc. Chem. Res., 1977, 10, 239.
9. V. I. Shvets, Russian Chem. Rev., 1974, 43, 488.
10. Solvent polarity is defined as polarity index, P', which is a measure of the ability of the solvent to interact with various polar test solutes. P' for Pyridine = 5.3, Pyridine-toluene(1:1) = 3.9, Pyridine-DMF(1:1) = 5.9, Pyridine-water(9:1) = 5.8, Pyridine-water(8:2) = 6.3, THF = 4.0, DMF = 6.4 (see ref. 11).
11. L. R. Snyder, J. Chromatogr., 1974, 92, 223.
12. From the X-ray crystal structure of 3, the distances of O1-O2 for cis-migration and O3-O4 for trans-migration are found to be 2.800 Å and somewhat longer 2.875 A, respectively.
13. S. K. Chung and Y. T. Chang, J. Chem. Soc. Chem. Commun., 1995, 13.
14. S. K. Chung and Y. Ryu, Carbohydr. Chem., 1994, 258, 145.
15. D. C. Billington and R. Baker, J. Chem. Soc. Chem. Commun., 1987, 1011.
16. V. G. S. Vox, Heterocycles, 1982, 19, 1932.
17. S. K. Chung, Y. Ryu, Y. T. Chang, D. Whang and K. Kim, Carbohydr. Res., 1994, 255, 13.
18. S. J. Cho, K. S. Kim and S. K. Chung, unpublished results.