Observations on the activation of methyl thioglycosides by iodine and its interhalogen compounds

Tetrahedron Asymmetry

Volumn 11, Issue 2, 2000, Pages 581-593

  Kartha, K P Ravindranathan ^a   Cura, Peter ^a   Aloui, Mahmoud ^a   Readman, S Kristy ^a   Rutherford, Trevor J ^a   Field, Robert A ^a  

^a UNIVERSITY OF ST ANDREWS   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

IODINE; IODINE DERIVATIVE; THIOGLYCOSIDE;

ARTICLE; GLYCOSYLATION; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0034635616     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00501-7     Document Type: Article

References (35)

1. Iodine and its interhalogen compounds: Versatile reagents in carbohydrate chemistry XI. For part X, see: Rutherford, T. J.; Kartha, K. P. R.; Readman, S. K.; Cura, P.; Field, R. A. Tetrahedron Lett. 1999, 40, 2025-2028.
2. Presented in part at the XVIII International Carbohydrate Symposium, Milan, Italy, 1996 (abstract BO 57 and BP 271) and at the XIX International Carbohydrate Symposium, San Diego, USA, 1998 (abstract BP 156).
3. Presented in part at the XVIII International Carbohydrate Symposium, Milan, Italy, 1996 (abstract BO 57 and BP 271) and at the XIX International Carbohydrate Symposium, San Diego, USA, 1998 (abstract BP 156).
4. Paulsen, H. In Modern Methods in Carbohydrate Synthesis; Khan, S. H.; O'Neill, R. A., Eds.; Harwood Academic Publishers: Amsterdam, 1996; pp. 1-20.
5. For representative examples of studies on the mechanism of glycosylation reactions see the following articles and references cited therein: Wulff, G.; Rohle, G. Angew. Chem., Int. Ed. Engl. 1974, 13, 157-170; Igarashi, K. Adv. Carbohydr. Chem. Biochem. 1977, 34, 243-283; Paulsen, H. Angew. Chem., Int. Ed. Engl. 1982, 21 155-224; Schmidt, R. R. Angew. Chem., Int. Ed. Engl. 1986, 25, 212-235; Lemieux, R. U. Explorations with Sugars: How Sweet it Was; American Chemical Society: Washington, 1990; Fraser-Reid, B.; Wu, Z. F.; Andrews, C. W.; Skowronski, E.; Bowen, J. P. J. Am. Chem. Soc. 1991, 113, 1434-1435; Gervay, J. In Organic Synthesis: Theory and Applicatons; JAI Press: London, 1998; Vol. 4, pp. 121-153; Crich, D.; Cai, W. L. J. Org. Chem. 1999, 64, 4926-4930.
6. For representative examples of studies on the mechanism of glycosylation reactions see the following articles and references cited therein: Wulff, G.; Rohle, G. Angew. Chem., Int. Ed. Engl. 1974, 13, 157-170; Igarashi, K. Adv. Carbohydr. Chem. Biochem. 1977, 34, 243-283; Paulsen, H. Angew. Chem., Int. Ed. Engl. 1982, 21 155-224; Schmidt, R. R. Angew. Chem., Int. Ed. Engl. 1986, 25, 212-235; Lemieux, R. U. Explorations with Sugars: How Sweet it Was; American Chemical Society: Washington, 1990; Fraser-Reid, B.; Wu, Z. F.; Andrews, C. W.; Skowronski, E.; Bowen, J. P. J. Am. Chem. Soc. 1991, 113, 1434-1435; Gervay, J. In Organic Synthesis: Theory and Applicatons; JAI Press: London, 1998; Vol. 4, pp. 121-153; Crich, D.; Cai, W. L. J. Org. Chem. 1999, 64, 4926-4930.
7. For representative examples of studies on the mechanism of glycosylation reactions see the following articles and references cited therein: Wulff, G.; Rohle, G. Angew. Chem., Int. Ed. Engl. 1974, 13, 157-170; Igarashi, K. Adv. Carbohydr. Chem. Biochem. 1977, 34, 243-283; Paulsen, H. Angew. Chem., Int. Ed. Engl. 1982, 21 155-224; Schmidt, R. R. Angew. Chem., Int. Ed. Engl. 1986, 25, 212-235; Lemieux, R. U. Explorations with Sugars: How Sweet it Was; American Chemical Society: Washington, 1990; Fraser-Reid, B.; Wu, Z. F.; Andrews, C. W.; Skowronski, E.; Bowen, J. P. J. Am. Chem. Soc. 1991, 113, 1434-1435; Gervay, J. In Organic Synthesis: Theory and Applicatons; JAI Press: London, 1998; Vol. 4, pp. 121-153; Crich, D.; Cai, W. L. J. Org. Chem. 1999, 64, 4926-4930.
8. For representative examples of studies on the mechanism of glycosylation reactions see the following articles and references cited therein: Wulff, G.; Rohle, G. Angew. Chem., Int. Ed. Engl. 1974, 13, 157-170; Igarashi, K. Adv. Carbohydr. Chem. Biochem. 1977, 34, 243-283; Paulsen, H. Angew. Chem., Int. Ed. Engl. 1982, 21 155-224; Schmidt, R. R. Angew. Chem., Int. Ed. Engl. 1986, 25, 212-235; Lemieux, R. U. Explorations with Sugars: How Sweet it Was; American Chemical Society: Washington, 1990; Fraser-Reid, B.; Wu, Z. F.; Andrews, C. W.; Skowronski, E.; Bowen, J. P. J. Am. Chem. Soc. 1991, 113, 1434-1435; Gervay, J. In Organic Synthesis: Theory and Applicatons; JAI Press: London, 1998; Vol. 4, pp. 121-153; Crich, D.; Cai, W. L. J. Org. Chem. 1999, 64, 4926-4930.
9. For representative examples of studies on the mechanism of glycosylation reactions see the following articles and references cited therein: Wulff, G.; Rohle, G. Angew. Chem., Int. Ed. Engl. 1974, 13, 157-170; Igarashi, K. Adv. Carbohydr. Chem. Biochem. 1977, 34, 243-283; Paulsen, H. Angew. Chem., Int. Ed. Engl. 1982, 21 155-224; Schmidt, R. R. Angew. Chem., Int. Ed. Engl. 1986, 25, 212-235; Lemieux, R. U. Explorations with Sugars: How Sweet it Was; American Chemical Society: Washington, 1990; Fraser-Reid, B.; Wu, Z. F.; Andrews, C. W.; Skowronski, E.; Bowen, J. P. J. Am. Chem. Soc. 1991, 113, 1434-1435; Gervay, J. In Organic Synthesis: Theory and Applicatons; JAI Press: London, 1998; Vol. 4, pp. 121-153; Crich, D.; Cai, W. L. J. Org. Chem. 1999, 64, 4926-4930.
10. For representative examples of studies on the mechanism of glycosylation reactions see the following articles and references cited therein: Wulff, G.; Rohle, G. Angew. Chem., Int. Ed. Engl. 1974, 13, 157-170; Igarashi, K. Adv. Carbohydr. Chem. Biochem. 1977, 34, 243-283; Paulsen, H. Angew. Chem., Int. Ed. Engl. 1982, 21 155-224; Schmidt, R. R. Angew. Chem., Int. Ed. Engl. 1986, 25, 212-235; Lemieux, R. U. Explorations with Sugars: How Sweet it Was; American Chemical Society: Washington, 1990; Fraser-Reid, B.; Wu, Z. F.; Andrews, C. W.; Skowronski, E.; Bowen, J. P. J. Am. Chem. Soc. 1991, 113, 1434-1435; Gervay, J. In Organic Synthesis: Theory and Applicatons; JAI Press: London, 1998; Vol. 4, pp. 121-153; Crich, D.; Cai, W. L. J. Org. Chem. 1999, 64, 4926-4930.
11. For representative examples of studies on the mechanism of glycosylation reactions see the following articles and references cited therein: Wulff, G.; Rohle, G. Angew. Chem., Int. Ed. Engl. 1974, 13, 157-170; Igarashi, K. Adv. Carbohydr. Chem. Biochem. 1977, 34, 243-283; Paulsen, H. Angew. Chem., Int. Ed. Engl. 1982, 21 155-224; Schmidt, R. R. Angew. Chem., Int. Ed. Engl. 1986, 25, 212-235; Lemieux, R. U. Explorations with Sugars: How Sweet it Was; American Chemical Society: Washington, 1990; Fraser-Reid, B.; Wu, Z. F.; Andrews, C. W.; Skowronski, E.; Bowen, J. P. J. Am. Chem. Soc. 1991, 113, 1434-1435; Gervay, J. In Organic Synthesis: Theory and Applicatons; JAI Press: London, 1998; Vol. 4, pp. 121-153; Crich, D.; Cai, W. L. J. Org. Chem. 1999, 64, 4926-4930.
12. For representative examples of studies on the mechanism of glycosylation reactions see the following articles and references cited therein: Wulff, G.; Rohle, G. Angew. Chem., Int. Ed. Engl. 1974, 13, 157-170; Igarashi, K. Adv. Carbohydr. Chem. Biochem. 1977, 34, 243-283; Paulsen, H. Angew. Chem., Int. Ed. Engl. 1982, 21 155-224; Schmidt, R. R. Angew. Chem., Int. Ed. Engl. 1986, 25, 212-235; Lemieux, R. U. Explorations with Sugars: How Sweet it Was; American Chemical Society: Washington, 1990; Fraser-Reid, B.; Wu, Z. F.; Andrews, C. W.; Skowronski, E.; Bowen, J. P. J. Am. Chem. Soc. 1991, 113, 1434-1435; Gervay, J. In Organic Synthesis: Theory and Applicatons; JAI Press: London, 1998; Vol. 4, pp. 121-153; Crich, D.; Cai, W. L. J. Org. Chem. 1999, 64, 4926-4930.
13. For review articles on the preparation of glycosyl halides and thioglycosides and their use in glycosylation reactions, see: Modern Methods in Carbohydrate Synthesis; Khan, S. H.; O'Neill, R. A.; Eds.; Harwood Academic Publishers: Chichester, 1996; Garegg, P. J. Adv. Carbohydr. Chem. Biochem. 1997, 52, 179.
14. For review articles on the preparation of glycosyl halides and thioglycosides and their use in glycosylation reactions, see: Modern Methods in Carbohydrate Synthesis; Khan, S. H.; O'Neill, R. A.; Eds.; Harwood Academic Publishers: Chichester, 1996; Garegg, P. J. Adv. Carbohydr. Chem. Biochem. 1997, 52, 179.
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32. Refs. 5, 6 and 14 above and the references cited within; Kartha, K. P. R.; Field, R. A. J. Carbohydr. Chem. 1998, 17, 693-702 and the references cited within; Lemieux, R. U. In Methods in Carbohydrate Chem. 2; Whistler, R. L.; Wolfrom, M. L., Eds.; Academic Press: New York, 1963, pp. 223-225; Pacsu, E.; Janson, J.; Lindberg, B. In Methods in Carbohydrate Chem. 2; Whistler, R. L.; Wolfrom, M. L., Eds.; Academic Press: New York, 1963; pp. 376-385; Paulsen, H. In Methods in Carbohydrate Chem. 6; Whistler, R. L.; Wolfrom, M. L., Eds.; Academic Press: New York, 1972; pp. 142-149.
33. Refs. 5, 6 and 14 above and the references cited within; Kartha, K. P. R.; Field, R. A. J. Carbohydr. Chem. 1998, 17, 693-702 and the references cited within; Lemieux, R. U. In Methods in Carbohydrate Chem. 2; Whistler, R. L.; Wolfrom, M. L., Eds.; Academic Press: New York, 1963, pp. 223-225; Pacsu, E.; Janson, J.; Lindberg, B. In Methods in Carbohydrate Chem. 2; Whistler, R. L.; Wolfrom, M. L., Eds.; Academic Press: New York, 1963; pp. 376-385; Paulsen, H. In Methods in Carbohydrate Chem. 6; Whistler, R. L.; Wolfrom, M. L., Eds.; Academic Press: New York, 1972; pp. 142-149.
34. Refs. 5, 6 and 14 above and the references cited within; Kartha, K. P. R.; Field, R. A. J. Carbohydr. Chem. 1998, 17, 693-702 and the references cited within; Lemieux, R. U. In Methods in Carbohydrate Chem. 2; Whistler, R. L.; Wolfrom, M. L., Eds.; Academic Press: New York, 1963, pp. 223-225; Pacsu, E.; Janson, J.; Lindberg, B. In Methods in Carbohydrate Chem. 2; Whistler, R. L.; Wolfrom, M. L., Eds.; Academic Press: New York, 1963; pp. 376-385; Paulsen, H. In Methods in Carbohydrate Chem. 6; Whistler, R. L.; Wolfrom, M. L., Eds.; Academic Press: New York, 1972; pp. 142-149.
35. Refs. 5, 6 and 14 above and the references cited within; Kartha, K. P. R.; Field, R. A. J. Carbohydr. Chem. 1998, 17, 693-702 and the references cited within; Lemieux, R. U. In Methods in Carbohydrate Chem. 2; Whistler, R. L.; Wolfrom, M. L., Eds.; Academic Press: New York, 1963, pp. 223-225; Pacsu, E.; Janson, J.; Lindberg, B. In Methods in Carbohydrate Chem. 2; Whistler, R. L.; Wolfrom, M. L., Eds.; Academic Press: New York, 1963; pp. 376-385; Paulsen, H. In Methods in Carbohydrate Chem. 6; Whistler, R. L.; Wolfrom, M. L., Eds.; Academic Press: New York, 1972; pp. 142-149.