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Volumn 61, Issue 15, 1996, Pages 5024-5031

The chemistry of isopropenyl glycopyranosides. Transglycosylations and other reactions

Author keywords

[No Author keywords available]

Indexed keywords

GLYCOSIDE;

EID: 0030054537     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960190p     Document Type: Article
Times cited : (44)

References (98)
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    • It is unclear whether the stereoselective formation of 10a-f is due to neighboring-group participation or a concerted mechanism with a cyclic transition state in which mercury coordinates the departing halide and delivers the enolate nucleophile from the opposite face of the pyranose ring. The reaction of 9c with inversion suggests a concerted mechanism, but reaction of 9f (α:β = 1:1) to give exclusively β glycoside might suggest neighboring-group participation. The unusually low yield of 10f, however, leaves open the possibility that only the α anomer of 9f reacted successfully to give 10f and that it did so by a concerted mechanism.
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    • For examples of electrophilic addition to glycosyl enol ethers or formation of glycosyl acetals, see: (a) Reference 20. (b) Koto, S.; Inada, S.; Narita, T.; Morishima, N.; Zen, S. Bull. Chem. Soc. Jpn. 1982, 55, 3665-3666. (c) Tietze, L. F.; Seele, R.; Leiting, B.; Krach, T. Carbohydr. Res. 1988, 180, 253-262. (d) Lehmann, J.; Ziser, L. Carbohydr. Res. 1988, 183, 301-309. (e) Barrett, A. G. M.; Bezuidenhoudt, B. C. B.; Gasiecki, A. F.; Howell, A. R.; Russell, M. A. J. Am. Chem. Soc. 1989, 111, 1392-1396. (f) Tietze, L. F.; Beller, M. Angew. Chem., Int. Ed. Engl. 1991, 30, 868-869.
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    • For examples of electrophilic addition to glycosyl enol ethers or formation of glycosyl acetals, see: (a) Reference 20. (b) Koto, S.; Inada, S.; Narita, T.; Morishima, N.; Zen, S. Bull. Chem. Soc. Jpn. 1982, 55, 3665-3666. (c) Tietze, L. F.; Seele, R.; Leiting, B.; Krach, T. Carbohydr. Res. 1988, 180, 253-262. (d) Lehmann, J.; Ziser, L. Carbohydr. Res. 1988, 183, 301-309. (e) Barrett, A. G. M.; Bezuidenhoudt, B. C. B.; Gasiecki, A. F.; Howell, A. R.; Russell, M. A. J. Am. Chem. Soc. 1989, 111, 1392-1396. (f) Tietze, L. F.; Beller, M. Angew. Chem., Int. Ed. Engl. 1991, 30, 868-869.
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    • Specific (covalent) complexation of the glycosyl cation intermediate would have led to the enhanced formation of hydrolysis product or tert-butyl glycoside, not the observed disaccharide.
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    • For intramolecular glycosyl delivery via acetal rearrangement, see: (a) Ito, Y.; Ogawa, T. Angew. Chem., Int. Ed. Engl. 1994, 33, 1765-1767. For intramolecular glycosyl delivery via orthoester rearrangement, see: (b) Reference 28. (c) Gass, J.; Strobl, M.; Loibner, A.; Kosma, P.; Zähringer, U. Carbohydr. Res. 1993, 244, 69-84. (d) Sznaidman, M. L.; Johnson, S. C.; Crasto, C.; Hecht, S. M. J. Org. Chem. 1995, 60, 3942-3943.
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    • For intramolecular glycosyl delivery via acetal rearrangement, see: (a) Ito, Y.; Ogawa, T. Angew. Chem., Int. Ed. Engl. 1994, 33, 1765-1767. For intramolecular glycosyl delivery via orthoester rearrangement, see: (b) Reference 28. (c) Gass, J.; Strobl, M.; Loibner, A.; Kosma, P.; Zähringer, U. Carbohydr. Res. 1993, 244, 69-84. (d) Sznaidman, M. L.; Johnson, S. C.; Crasto, C.; Hecht, S. M. J. Org. Chem. 1995, 60, 3942-3943.
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    • For intramolecular glycosyl delivery via acetal rearrangement, see: (a) Ito, Y.; Ogawa, T. Angew. Chem., Int. Ed. Engl. 1994, 33, 1765-1767. For intramolecular glycosyl delivery via orthoester rearrangement, see: (b) Reference 28. (c) Gass, J.; Strobl, M.; Loibner, A.; Kosma, P.; Zähringer, U. Carbohydr. Res. 1993, 244, 69-84. (d) Sznaidman, M. L.; Johnson, S. C.; Crasto, C.; Hecht, S. M. J. Org. Chem. 1995, 60, 3942-3943.
    • (1993) Carbohydr. Res. , vol.244 , pp. 69-84
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    • For intramolecular glycosyl delivery via acetal rearrangement, see: (a) Ito, Y.; Ogawa, T. Angew. Chem., Int. Ed. Engl. 1994, 33, 1765-1767. For intramolecular glycosyl delivery via orthoester rearrangement, see: (b) Reference 28. (c) Gass, J.; Strobl, M.; Loibner, A.; Kosma, P.; Zähringer, U. Carbohydr. Res. 1993, 244, 69-84. (d) Sznaidman, M. L.; Johnson, S. C.; Crasto, C.; Hecht, S. M. J. Org. Chem. 1995, 60, 3942-3943.
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    • For discussions of electronically armed and disarmed glycosyl donors, see (a) Mootoo, D. R.; Konradsson, P.; Udodong, U.; Fraser-Reid, B. J. Am. Chem. Soc. 1988, 110, 5583-5584. (b) Friesen. R. W.; Danishefsky, S. J. J. Am. Chem. Soc. 1989, 111, 6656-6660. (c) Halcomb, R. L.; Danishefsky, S. J. J. Am. Chem. Soc. 1989, 111, 6661-6666. (d) Veeneman, G. H.; van Boom, J. H. Tetrahedron Lett. 1990, 31, 275-278.
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    • For discussions of electronically armed and disarmed glycosyl donors, see (a) Mootoo, D. R.; Konradsson, P.; Udodong, U.; Fraser-Reid, B. J. Am. Chem. Soc. 1988, 110, 5583-5584. (b) Friesen. R. W.; Danishefsky, S. J. J. Am. Chem. Soc. 1989, 111, 6656-6660. (c) Halcomb, R. L.; Danishefsky, S. J. J. Am. Chem. Soc. 1989, 111, 6661-6666. (d) Veeneman, G. H.; van Boom, J. H. Tetrahedron Lett. 1990, 31, 275-278.
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    • A similar result based on the differential reactivity of seleno-and thioglycosides has been reported: Mehta, S.; Pinto, B. M. Tetrahedron Lett. 1991, 32, 4435-4438.
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    • The use of ether as solvent is known to promote the formation of 1,2-cis-disaccharides: (a) Igarashi, K.; Irisawa, J.; Honma, T. Carbohydr. Res. 1975, 39, 213-225. (b) Reference 8. (c) Hashimoto, S.; Hayashi, M.; Noyori, R. Tetrahedron Lett. 1984, 25, 1379-1382. (d) Mukaiyama, T.; Katsurada, M.; Takashima, T. Chem. Lett. 1991, 985-988.
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    • Reference 8
    • The use of ether as solvent is known to promote the formation of 1,2-cis-disaccharides: (a) Igarashi, K.; Irisawa, J.; Honma, T. Carbohydr. Res. 1975, 39, 213-225. (b) Reference 8. (c) Hashimoto, S.; Hayashi, M.; Noyori, R. Tetrahedron Lett. 1984, 25, 1379-1382. (d) Mukaiyama, T.; Katsurada, M.; Takashima, T. Chem. Lett. 1991, 985-988.
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    • The use of ether as solvent is known to promote the formation of 1,2-cis-disaccharides: (a) Igarashi, K.; Irisawa, J.; Honma, T. Carbohydr. Res. 1975, 39, 213-225. (b) Reference 8. (c) Hashimoto, S.; Hayashi, M.; Noyori, R. Tetrahedron Lett. 1984, 25, 1379-1382. (d) Mukaiyama, T.; Katsurada, M.; Takashima, T. Chem. Lett. 1991, 985-988.
    • (1984) Tetrahedron Lett. , vol.25 , pp. 1379-1382
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    • The use of ether as solvent is known to promote the formation of 1,2-cis-disaccharides: (a) Igarashi, K.; Irisawa, J.; Honma, T. Carbohydr. Res. 1975, 39, 213-225. (b) Reference 8. (c) Hashimoto, S.; Hayashi, M.; Noyori, R. Tetrahedron Lett. 1984, 25, 1379-1382. (d) Mukaiyama, T.; Katsurada, M.; Takashima, T. Chem. Lett. 1991, 985-988.
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    • Tetraalkylammonium bromide salts promote the equilibration of α-glycosyl bromides to the more reactive β-glycosyl bromides, leading to stereoselective α-glycoside formation in dichloromethane: Lemieux, R. U.; Hendriks, K. B.; Stick, R. V.; James, K. J. Am. Chem. Soc. 1975, 97, 4056-4062.
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    • note
    • DMTST and TBAB have been used to promote the stereoselective formation of 1,2-cis-disaccharides, using thioglycosides as glycosyl donors. See reference 5.


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