Relative Nucleophilicity of the Two Sulfur Atoms in 1,5-Dithioglucopyranoside

Angewandte Chemie (International Edition in English)

Volumn 36, Issue 8, 1997, Pages 868-870

  Yuasa, Hideya ^a   Kamata, Yujiro ^a   Hashimoto, Hironobu ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Anomeric effect; Glycosides; Kinetics; Sulfur

Indexed keywords

EID: 0030942624     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199708681     Document Type: Article

References (26)

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2. b) R. U. Lemieux, Explorations with Sugars - How Sweet It Was, American Chemical Society, Washington, DC, 1990.
3. For reviews, see a) P. Deslongchamps, Stereoelectronic Effects in Organic Chemistry, Pergamon, New York, 1983; b) A. J. Kirby, The Anomeric Effect and Related Stereoelectronic Effects at Oxygen, Springer, New York, 1983; c) I. Tvaroska, T. Bleha, Adv. Carbohydr. Chem. Biochem. 1989, 47, 45-123; d) E. Juaristi, G. Cuevas, Tetrahedron 1992, 48, 5019-5087; e) The Anomeric Effect and Associated Stereoelectronic Effects (Ed.: G. R. Thatcher), American Chemical Society, Washington, DC, 1993 (ACS Symp. Ser. 1993, 539).
4. For reviews, see a) P. Deslongchamps, Stereoelectronic Effects in Organic Chemistry, Pergamon, New York, 1983; b) A. J. Kirby, The Anomeric Effect and Related Stereoelectronic Effects at Oxygen, Springer, New York, 1983; c) I. Tvaroska, T. Bleha, Adv. Carbohydr. Chem. Biochem. 1989, 47, 45-123; d) E. Juaristi, G. Cuevas, Tetrahedron 1992, 48, 5019-5087; e) The Anomeric Effect and Associated Stereoelectronic Effects (Ed.: G. R. Thatcher), American Chemical Society, Washington, DC, 1993 (ACS Symp. Ser. 1993, 539).
5. For reviews, see a) P. Deslongchamps, Stereoelectronic Effects in Organic Chemistry, Pergamon, New York, 1983; b) A. J. Kirby, The Anomeric Effect and Related Stereoelectronic Effects at Oxygen, Springer, New York, 1983; c) I. Tvaroska, T. Bleha, Adv. Carbohydr. Chem. Biochem. 1989, 47, 45-123; d) E. Juaristi, G. Cuevas, Tetrahedron 1992, 48, 5019-5087; e) The Anomeric Effect and Associated Stereoelectronic Effects (Ed.: G. R. Thatcher), American Chemical Society, Washington, DC, 1993 (ACS Symp. Ser. 1993, 539).
6. For reviews, see a) P. Deslongchamps, Stereoelectronic Effects in Organic Chemistry, Pergamon, New York, 1983; b) A. J. Kirby, The Anomeric Effect and Related Stereoelectronic Effects at Oxygen, Springer, New York, 1983; c) I. Tvaroska, T. Bleha, Adv. Carbohydr. Chem. Biochem. 1989, 47, 45-123; d) E. Juaristi, G. Cuevas, Tetrahedron 1992, 48, 5019-5087; e) The Anomeric Effect and Associated Stereoelectronic Effects (Ed.: G. R. Thatcher), American Chemical Society, Washington, DC, 1993 (ACS Symp. Ser. 1993, 539).
7. For reviews, see a) P. Deslongchamps, Stereoelectronic Effects in Organic Chemistry, Pergamon, New York, 1983; b) A. J. Kirby, The Anomeric Effect and Related Stereoelectronic Effects at Oxygen, Springer, New York, 1983; c) I. Tvaroska, T. Bleha, Adv. Carbohydr. Chem. Biochem. 1989, 47, 45-123; d) E. Juaristi, G. Cuevas, Tetrahedron 1992, 48, 5019-5087; e) The Anomeric Effect and Associated Stereoelectronic Effects (Ed.: G. R. Thatcher), American Chemical Society, Washington, DC, 1993 (ACS Symp. Ser. 1993, 539).
8. For reviews, see a) P. Deslongchamps, Stereoelectronic Effects in Organic Chemistry, Pergamon, New York, 1983; b) A. J. Kirby, The Anomeric Effect and Related Stereoelectronic Effects at Oxygen, Springer, New York, 1983; c) I. Tvaroska, T. Bleha, Adv. Carbohydr. Chem. Biochem. 1989, 47, 45-123; d) E. Juaristi, G. Cuevas, Tetrahedron 1992, 48, 5019-5087; e) The Anomeric Effect and Associated Stereoelectronic Effects (Ed.: G. R. Thatcher), American Chemical Society, Washington, DC, 1993 (ACS Symp. Ser. 1993, 539).
9. C. L. Perrin, K. B. Armstrong, M. A. Fabian, J. Am. Chem. Soc. 1994, 116, 715-722, and references therein.
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14. H. Hashimoto, M. Kawanishi, H. Yuasa, Carbohydr. Res. 1996, 282, 207-221.
15. The n-σ* hypothesis cannot easily explain the solvent effects for the equilibrium between two conformers of C1-substituted tetrahydropyrans. See refs. [3, 8] for a discussion of the solvent effects.
16. J.-P. Praly, R. U. Lemieux, Can. J. Chem. 1987, 65, 213-223.
17. C. W. Andrews, J. P. Bowen, B. Fraser-Reid, J. Chem. Soc. Chem. Commun. 1989, 1913-1916.
18. For the protonation of hydroxyl groups, see B. Gillet, D. J. Nicole, J.-J. Delpuech, J. Chem. Soc., Perkin Trans. 2 1981, 1329-1335.
19. B. M. Pinto, R. Y. N. Leung in ref. [2e], pp. 126-155.
20. H. Yuasa, H. Hashimoto, Tetrahedron 1993, 49, 8977-8998.
21. Only the sulfoxides were produced during the measurements; the ratio of products with axial and equatorial sulfoxide groups was 2.5-5.3 for the α-glycosides and 0.4-0.6 for the β-glycosides. The stereoselectivity of the oxidation of α-glycosides has been discussed in ref. [12]. Details will be reported elsewhere.
22. C. Hansch, A. Leo, R. W. Taft, Chem. Rev. 1991, 91, 165-195.
23. a) R. B. Gupta, R. W. Franck, J. Am. Chem. Soc. 1987, 109, 6554-6556;
24. b) D. R. McPhail, J. R. Lee, B. Fraser-Reid, ibid. 1992, 114, 1905-1906;
25. c) J. L. Liras, E. V. Anslyn, ibid. 1994, 116, 2645-2646.
26. The consistency may be fortuitous, because not only the protonation equilibrium but also the C-O cleavage step is critical for the apparent rate in the acid-catalyzed acetal hydrolysis.