Stereoselectivity in Glycosidic Bond Formation: Studies on the Anomerisation of Thioglycosides

Synlett

Volumn 1996, Issue 9, 1996, Pages 906-908

  Boons, Geert Jan ^a   Stauch, Thomas ^a  

^a UNIVERSITY OF BIRMINGHAM   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002977385     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5610     Document Type: Article

References (26)

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5. b) H. Paulsen, ibid, 29 (1990) 823;
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8. e) P. Sinay, ibid, 63 (1991) 519;
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10. g) A. Vasella, ibid, 63 (1991) 507,
11. h) B. Fraser-Reid, U.E. Udodong, Z. Wu, H. Ottoson, J.R. Merritt, S. Rao, C. Roberts, R. Madsen, Synlett, 12 (1992) 927;
12. i) P. Fugedi, P.J. Garegg, H. Lohn, T. Norberg, Glycoconjugate J., 4 (1987) 97;
13. j) K. Toshima, K. Tasuta, Chem. Rev., 93 (1993) 1503;
14. k) G.J. Boons, Tetrahedron, 52 (1996) 1095.
15. Iodonium-ion mediated glycosylation of thioglycosides give in particular high α-selectivities G.H. Veeneman, J.H. van Boom, Tetrahedron Lett., 31 (1990) 275.
16. 1H NMR-spectroscopy and similar anomeric ratios were observed as presented by the quenching approach. The rate of exchange, however, was too fast to obtain kinetic data.
17. A similar finding has been observation by Veeneman; G. Veeneman, Thesis, Leiden, The Netherlands (1991)
18. S. Masamune, W. Chog, J.S. Pedersen, L.R. Sita, Angew. Chem. Int. Ed. Engl., 24 (1985) 1.
19. The collidine, perchlorate-anion or solvent may be associated with a carboxonium ion therefore the term carboxonium-like-ion is more appropriate.
20. a) M. Cerny L Pacak, Coll. Czech. Chem. Commun., 24 (1959) 2566;
21. b) D. Horton, Methods Carbohydr. Chem., 2 (1963) 4333;
22. c) F.D. Tropper, F.O. Andersson, C. Grand-Maite, R. Roy, Synthesis, (1991) 734;
23. c) R.R. Schmidt, M. Stumpp, Liebigs Ann. Chem., (1983) 1249;
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25. f) S. Bennett, M. von Itzstein, M.J. Kiefel, Carbohydrate Res., 259 (1994) 293.
26. tbutylsulfenyl iodide may be too stable to release an iodonium-ion and the reaction is not catalytic. When the carboxonium-ion reacts with an alcohol, the sulfenyl iodide will react with alkyl sulfide to give a disulfide and iodine. Thus, during glycosylation the reaction is not catalytic in IDCP.