Template directed cyclo-glycosylation: Effect of the anchoring sites of the spacer and temperature in the regio-and stereo-selectivity of the glycosylation

Tetrahedron Letters

Volumn 37, Issue 7, 1996, Pages 1105-1108

  Valverde, Serafín ^a   Gómez, Ana M ^a   López, J Cristóbal ^a   Herradón, Bernardo ^a  

^a INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

DISACCHARIDE;

ARTICLE; CARBOHYDRATE SYNTHESIS; GLYCOSYLATION; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030019874     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02316-X     Document Type: Article

References (32)

1. For reviews, see: Bochkov, A.-F.; Zaikov G. E. Chemistry of the O-Glycosidic Bond: Formation and Cleavage; Pergamon Press, Oxford, 1979; Paulsen, H. Angew. Chem., Int. Ed. Eng., 1982, 27, 155-173; Schmidt, R. R. Angew. Chem., Int. Ed. Eng., 1986, 25, 212-235; Kunz, H. Angew. Chem., Int. Ed. Eng., 1987, 26, 294-308; Paulsen, H. Angew. Chem., Int. Ed. Eng., 1990, 29, 823-839; Schmidt, R. R. in Comprehensive Organic Synthesis; Pergamon Press: Oxford, 1991; Vol 6, p 33-64; Sinaÿ, P. Pure Appl. Chem., 1991, 63, 519-528; Garegg, P. J. Acc. Chem. Res., 1992, 25, 575-580; Toshima, K.; Tatsuta, K. Chem. Rev., 1993, 93, 1503-1531.
2. For reviews, see: Bochkov, A.-F.; Zaikov G. E. Chemistry of the O-Glycosidic Bond: Formation and Cleavage; Pergamon Press, Oxford, 1979; Paulsen, H. Angew. Chem., Int. Ed. Eng., 1982, 27, 155-173; Schmidt, R. R. Angew. Chem., Int. Ed. Eng., 1986, 25, 212-235; Kunz, H. Angew. Chem., Int. Ed. Eng., 1987, 26, 294-308; Paulsen, H. Angew. Chem., Int. Ed. Eng., 1990, 29, 823-839; Schmidt, R. R. in Comprehensive Organic Synthesis; Pergamon Press: Oxford, 1991; Vol 6, p 33-64; Sinaÿ, P. Pure Appl. Chem., 1991, 63, 519-528; Garegg, P. J. Acc. Chem. Res., 1992, 25, 575-580; Toshima, K.; Tatsuta, K. Chem. Rev., 1993, 93, 1503-1531.
3. For reviews, see: Bochkov, A.-F.; Zaikov G. E. Chemistry of the O-Glycosidic Bond: Formation and Cleavage; Pergamon Press, Oxford, 1979; Paulsen, H. Angew. Chem., Int. Ed. Eng., 1982, 27, 155-173; Schmidt, R. R. Angew. Chem., Int. Ed. Eng., 1986, 25, 212-235; Kunz, H. Angew. Chem., Int. Ed. Eng., 1987, 26, 294-308; Paulsen, H. Angew. Chem., Int. Ed. Eng., 1990, 29, 823-839; Schmidt, R. R. in Comprehensive Organic Synthesis; Pergamon Press: Oxford, 1991; Vol 6, p 33-64; Sinaÿ, P. Pure Appl. Chem., 1991, 63, 519-528; Garegg, P. J. Acc. Chem. Res., 1992, 25, 575-580; Toshima, K.; Tatsuta, K. Chem. Rev., 1993, 93, 1503-1531.
4. For reviews, see: Bochkov, A.-F.; Zaikov G. E. Chemistry of the O-Glycosidic Bond: Formation and Cleavage; Pergamon Press, Oxford, 1979; Paulsen, H. Angew. Chem., Int. Ed. Eng., 1982, 27, 155-173; Schmidt, R. R. Angew. Chem., Int. Ed. Eng., 1986, 25, 212-235; Kunz, H. Angew. Chem., Int. Ed. Eng., 1987, 26, 294-308; Paulsen, H. Angew. Chem., Int. Ed. Eng., 1990, 29, 823-839; Schmidt, R. R. in Comprehensive Organic Synthesis; Pergamon Press: Oxford, 1991; Vol 6, p 33-64; Sinaÿ, P. Pure Appl. Chem., 1991, 63, 519-528; Garegg, P. J. Acc. Chem. Res., 1992, 25, 575-580; Toshima, K.; Tatsuta, K. Chem. Rev., 1993, 93, 1503-1531.
5. For reviews, see: Bochkov, A.-F.; Zaikov G. E. Chemistry of the O-Glycosidic Bond: Formation and Cleavage; Pergamon Press, Oxford, 1979; Paulsen, H. Angew. Chem., Int. Ed. Eng., 1982, 27, 155-173; Schmidt, R. R. Angew. Chem., Int. Ed. Eng., 1986, 25, 212-235; Kunz, H. Angew. Chem., Int. Ed. Eng., 1987, 26, 294-308; Paulsen, H. Angew. Chem., Int. Ed. Eng., 1990, 29, 823-839; Schmidt, R. R. in Comprehensive Organic Synthesis; Pergamon Press: Oxford, 1991; Vol 6, p 33-64; Sinaÿ, P. Pure Appl. Chem., 1991, 63, 519-528; Garegg, P. J. Acc. Chem. Res., 1992, 25, 575-580; Toshima, K.; Tatsuta, K. Chem. Rev., 1993, 93, 1503-1531.
6. For reviews, see: Bochkov, A.-F.; Zaikov G. E. Chemistry of the O-Glycosidic Bond: Formation and Cleavage; Pergamon Press, Oxford, 1979; Paulsen, H. Angew. Chem., Int. Ed. Eng., 1982, 27, 155-173; Schmidt, R. R. Angew. Chem., Int. Ed. Eng., 1986, 25, 212-235; Kunz, H. Angew. Chem., Int. Ed. Eng., 1987, 26, 294-308; Paulsen, H. Angew. Chem., Int. Ed. Eng., 1990, 29, 823-839; Schmidt, R. R. in Comprehensive Organic Synthesis; Pergamon Press: Oxford, 1991; Vol 6, p 33-64; Sinaÿ, P. Pure Appl. Chem., 1991, 63, 519-528; Garegg, P. J. Acc. Chem. Res., 1992, 25, 575-580; Toshima, K.; Tatsuta, K. Chem. Rev., 1993, 93, 1503-1531.
7. For reviews, see: Bochkov, A.-F.; Zaikov G. E. Chemistry of the O-Glycosidic Bond: Formation and Cleavage; Pergamon Press, Oxford, 1979; Paulsen, H. Angew. Chem., Int. Ed. Eng., 1982, 27, 155-173; Schmidt, R. R. Angew. Chem., Int. Ed. Eng., 1986, 25, 212-235; Kunz, H. Angew. Chem., Int. Ed. Eng., 1987, 26, 294-308; Paulsen, H. Angew. Chem., Int. Ed. Eng., 1990, 29, 823-839; Schmidt, R. R. in Comprehensive Organic Synthesis; Pergamon Press: Oxford, 1991; Vol 6, p 33-64; Sinaÿ, P. Pure Appl. Chem., 1991, 63, 519-528; Garegg, P. J. Acc. Chem. Res., 1992, 25, 575-580; Toshima, K.; Tatsuta, K. Chem. Rev., 1993, 93, 1503-1531.
8. For reviews, see: Bochkov, A.-F.; Zaikov G. E. Chemistry of the O-Glycosidic Bond: Formation and Cleavage; Pergamon Press, Oxford, 1979; Paulsen, H. Angew. Chem., Int. Ed. Eng., 1982, 27, 155-173; Schmidt, R. R. Angew. Chem., Int. Ed. Eng., 1986, 25, 212-235; Kunz, H. Angew. Chem., Int. Ed. Eng., 1987, 26, 294-308; Paulsen, H. Angew. Chem., Int. Ed. Eng., 1990, 29, 823-839; Schmidt, R. R. in Comprehensive Organic Synthesis; Pergamon Press: Oxford, 1991; Vol 6, p 33-64; Sinaÿ, P. Pure Appl. Chem., 1991, 63, 519-528; Garegg, P. J. Acc. Chem. Res., 1992, 25, 575-580; Toshima, K.; Tatsuta, K. Chem. Rev., 1993, 93, 1503-1531.
9. For reviews, see: Bochkov, A.-F.; Zaikov G. E. Chemistry of the O-Glycosidic Bond: Formation and Cleavage; Pergamon Press, Oxford, 1979; Paulsen, H. Angew. Chem., Int. Ed. Eng., 1982, 27, 155-173; Schmidt, R. R. Angew. Chem., Int. Ed. Eng., 1986, 25, 212-235; Kunz, H. Angew. Chem., Int. Ed. Eng., 1987, 26, 294-308; Paulsen, H. Angew. Chem., Int. Ed. Eng., 1990, 29, 823-839; Schmidt, R. R. in Comprehensive Organic Synthesis; Pergamon Press: Oxford, 1991; Vol 6, p 33-64; Sinaÿ, P. Pure Appl. Chem., 1991, 63, 519-528; Garegg, P. J. Acc. Chem. Res., 1992, 25, 575-580; Toshima, K.; Tatsuta, K. Chem. Rev., 1993, 93, 1503-1531.
10. For recent methods of chemical glycosylation: Mootoo, D. R.; Konradsson, P.; Udodong, U.; Fraser-Reid, B. J. Am. Chem. Soc., 1988, 110, 5583-5584; Kirchner, E.; Thiem, F.; Dernick, R.; Heukeshoven, J.; Thiem, J. J. Carbohydr. Chem., 1988, 7, 453-486; Nicolaou, K. C.; Caufield, T.; Kataoka, H.; Kumazawa, P. J. Am. Chem. Soc., 1988, 110, 7910-7912; 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; Friesen, R. W.; Danishefsky, S. J. Am. Chem. Soc., 1989, 111, 6656-6660; Halcomb, R. L.; Danishefsky, S. J. Am. Chem. Soc., 1989, 111, 6661-6666; Kahne, D.; Walker, S.; Cheng, Y.; van Engen, D. J. Am. Chem. Soc., 1989, 111, 6881-6882; Briner, K.; Vasella, A, Helv. Chim. Acta 1989, 72, 1371-1382; Kunz, H.; Wernig, P.; Schultz, M. Synlett 1990, 631-632; López, J. C; Fraser-Reid, B. J. Chem. Soc., Chem. Commun., 1991, 159-161; Barressi, F.; Hindsgaul, O. J. Am. Chem. Soc., 1991, 113, 9376-9377; Stork, G.; Kim, G. J. Am. Chem. Soc., 1992, 114, 1087-1088; Bols, M. Tetrahedron 1993, 49, 10049-10060; Ito, Y.; Ogawa, T. Angew. Chem., Int. Ed. Eng., 1994, 33, 1765-1767; Kondo, H.; Aoki, S.; Ichikawa, Y.; Halcomb, R. L.; Ritzen, H.; Wong, C.-H. J. Org. Chem., 1994, 59, 864-877;
11. For recent methods of chemical glycosylation: Mootoo, D. R.; Konradsson, P.; Udodong, U.; Fraser-Reid, B. J. Am. Chem. Soc., 1988, 110, 5583-5584; Kirchner, E.; Thiem, F.; Dernick, R.; Heukeshoven, J.; Thiem, J. J. Carbohydr. Chem., 1988, 7, 453-486; Nicolaou, K. C.; Caufield, T.; Kataoka, H.; Kumazawa, P. J. Am. Chem. Soc., 1988, 110, 7910-7912; 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; Friesen, R. W.; Danishefsky, S. J. Am. Chem. Soc., 1989, 111, 6656-6660; Halcomb, R. L.; Danishefsky, S. J. Am. Chem. Soc., 1989, 111, 6661-6666; Kahne, D.; Walker, S.; Cheng, Y.; van Engen, D. J. Am. Chem. Soc., 1989, 111, 6881-6882; Briner, K.; Vasella, A, Helv. Chim. Acta 1989, 72, 1371-1382; Kunz, H.; Wernig, P.; Schultz, M. Synlett 1990, 631-632; López, J. C; Fraser-Reid, B. J. Chem. Soc., Chem. Commun., 1991, 159-161; Barressi, F.; Hindsgaul, O. J. Am. Chem. Soc., 1991, 113, 9376-9377; Stork, G.; Kim, G. J. Am. Chem. Soc., 1992, 114, 1087-1088; Bols, M. Tetrahedron 1993, 49, 10049-10060; Ito, Y.; Ogawa, T. Angew. Chem., Int. Ed. Eng., 1994, 33, 1765-1767; Kondo, H.; Aoki, S.; Ichikawa, Y.; Halcomb, R. L.; Ritzen, H.; Wong, C.-H. J. Org. Chem., 1994, 59, 864-877;
12. For recent methods of chemical glycosylation: Mootoo, D. R.; Konradsson, P.; Udodong, U.; Fraser-Reid, B. J. Am. Chem. Soc., 1988, 110, 5583-5584; Kirchner, E.; Thiem, F.; Dernick, R.; Heukeshoven, J.; Thiem, J. J. Carbohydr. Chem., 1988, 7, 453-486; Nicolaou, K. C.; Caufield, T.; Kataoka, H.; Kumazawa, P. J. Am. Chem. Soc., 1988, 110, 7910-7912; 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; Friesen, R. W.; Danishefsky, S. J. Am. Chem. Soc., 1989, 111, 6656-6660; Halcomb, R. L.; Danishefsky, S. J. Am. Chem. Soc., 1989, 111, 6661-6666; Kahne, D.; Walker, S.; Cheng, Y.; van Engen, D. J. Am. Chem. Soc., 1989, 111, 6881-6882; Briner, K.; Vasella, A, Helv. Chim. Acta 1989, 72, 1371-1382; Kunz, H.; Wernig, P.; Schultz, M. Synlett 1990, 631-632; López, J. C; Fraser-Reid, B. J. Chem. Soc., Chem. Commun., 1991, 159-161; Barressi, F.; Hindsgaul, O. J. Am. Chem. Soc., 1991, 113, 9376-9377; Stork, G.; Kim, G. J. Am. Chem. Soc., 1992, 114, 1087-1088; Bols, M. Tetrahedron 1993, 49, 10049-10060; Ito, Y.; Ogawa, T. Angew. Chem., Int. Ed. Eng., 1994, 33, 1765-1767; Kondo, H.; Aoki, S.; Ichikawa, Y.; Halcomb, R. L.; Ritzen, H.; Wong, C.-H. J. Org. Chem., 1994, 59, 864-877;
13. For recent methods of chemical glycosylation: Mootoo, D. R.; Konradsson, P.; Udodong, U.; Fraser-Reid, B. J. Am. Chem. Soc., 1988, 110, 5583-5584; Kirchner, E.; Thiem, F.; Dernick, R.; Heukeshoven, J.; Thiem, J. J. Carbohydr. Chem., 1988, 7, 453-486; Nicolaou, K. C.; Caufield, T.; Kataoka, H.; Kumazawa, P. J. Am. Chem. Soc., 1988, 110, 7910-7912; 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; Friesen, R. W.; Danishefsky, S. J. Am. Chem. Soc., 1989, 111, 6656-6660; Halcomb, R. L.; Danishefsky, S. J. Am. Chem. Soc., 1989, 111, 6661-6666; Kahne, D.; Walker, S.; Cheng, Y.; van Engen, D. J. Am. Chem. Soc., 1989, 111, 6881-6882; Briner, K.; Vasella, A, Helv. Chim. Acta 1989, 72, 1371-1382; Kunz, H.; Wernig, P.; Schultz, M. Synlett 1990, 631-632; López, J. C; Fraser-Reid, B. J. Chem. Soc., Chem. Commun., 1991, 159-161; Barressi, F.; Hindsgaul, O. J. Am. Chem. Soc., 1991, 113, 9376-9377; Stork, G.; Kim, G. J. Am. Chem. Soc., 1992, 114, 1087-1088; Bols, M. Tetrahedron 1993, 49, 10049-10060; Ito, Y.; Ogawa, T. Angew. Chem., Int. Ed. Eng., 1994, 33, 1765-1767; Kondo, H.; Aoki, S.; Ichikawa, Y.; Halcomb, R. L.; Ritzen, H.; Wong, C.-H. J. Org. Chem., 1994, 59, 864-877;
14. For recent methods of chemical glycosylation: Mootoo, D. R.; Konradsson, P.; Udodong, U.; Fraser-Reid, B. J. Am. Chem. Soc., 1988, 110, 5583-5584; Kirchner, E.; Thiem, F.; Dernick, R.; Heukeshoven, J.; Thiem, J. J. Carbohydr. Chem., 1988, 7, 453-486; Nicolaou, K. C.; Caufield, T.; Kataoka, H.; Kumazawa, P. J. Am. Chem. Soc., 1988, 110, 7910-7912; 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; Friesen, R. W.; Danishefsky, S. J. Am. Chem. Soc., 1989, 111, 6656-6660; Halcomb, R. L.; Danishefsky, S. J. Am. Chem. Soc., 1989, 111, 6661-6666; Kahne, D.; Walker, S.; Cheng, Y.; van Engen, D. J. Am. Chem. Soc., 1989, 111, 6881-6882; Briner, K.; Vasella, A, Helv. Chim. Acta 1989, 72, 1371-1382; Kunz, H.; Wernig, P.; Schultz, M. Synlett 1990, 631-632; López, J. C; Fraser-Reid, B. J. Chem. Soc., Chem. Commun., 1991, 159-161; Barressi, F.; Hindsgaul, O. J. Am. Chem. Soc., 1991, 113, 9376-9377; Stork, G.; Kim, G. J. Am. Chem. Soc., 1992, 114, 1087-1088; Bols, M. Tetrahedron 1993, 49, 10049-10060; Ito, Y.; Ogawa, T. Angew. Chem., Int. Ed. Eng., 1994, 33, 1765-1767; Kondo, H.; Aoki, S.; Ichikawa, Y.; Halcomb, R. L.; Ritzen, H.; Wong, C.-H. J. Org. Chem., 1994, 59, 864-877;
15. For recent methods of chemical glycosylation: Mootoo, D. R.; Konradsson, P.; Udodong, U.; Fraser-Reid, B. J. Am. Chem. Soc., 1988, 110, 5583-5584; Kirchner, E.; Thiem, F.; Dernick, R.; Heukeshoven, J.; Thiem, J. J. Carbohydr. Chem., 1988, 7, 453-486; Nicolaou, K. C.; Caufield, T.; Kataoka, H.; Kumazawa, P. J. Am. Chem. Soc., 1988, 110, 7910-7912; 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; Friesen, R. W.; Danishefsky, S. J. Am. Chem. Soc., 1989, 111, 6656-6660; Halcomb, R. L.; Danishefsky, S. J. Am. Chem. Soc., 1989, 111, 6661-6666; Kahne, D.; Walker, S.; Cheng, Y.; van Engen, D. J. Am. Chem. Soc., 1989, 111, 6881-6882; Briner, K.; Vasella, A, Helv. Chim. Acta 1989, 72, 1371-1382; Kunz, H.; Wernig, P.; Schultz, M. Synlett 1990, 631-632; López, J. C; Fraser-Reid, B. J. Chem. Soc., Chem. Commun., 1991, 159-161; Barressi, F.; Hindsgaul, O. J. Am. Chem. Soc., 1991, 113, 9376-9377; Stork, G.; Kim, G. J. Am. Chem. Soc., 1992, 114, 1087-1088; Bols, M. Tetrahedron 1993, 49, 10049-10060; Ito, Y.; Ogawa, T. Angew. Chem., Int. Ed. Eng., 1994, 33, 1765-1767; Kondo, H.; Aoki, S.; Ichikawa, Y.; Halcomb, R. L.; Ritzen, H.; Wong, C.-H. J. Org. Chem., 1994, 59, 864-877;
16. For recent methods of chemical glycosylation: Mootoo, D. R.; Konradsson, P.; Udodong, U.; Fraser-Reid, B. J. Am. Chem. Soc., 1988, 110, 5583-5584; Kirchner, E.; Thiem, F.; Dernick, R.; Heukeshoven, J.; Thiem, J. J. Carbohydr. Chem., 1988, 7, 453-486; Nicolaou, K. C.; Caufield, T.; Kataoka, H.; Kumazawa, P. J. Am. Chem. Soc., 1988, 110, 7910-7912; 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; Friesen, R. W.; Danishefsky, S. J. Am. Chem. Soc., 1989, 111, 6656-6660; Halcomb, R. L.; Danishefsky, S. J. Am. Chem. Soc., 1989, 111, 6661-6666; Kahne, D.; Walker, S.; Cheng, Y.; van Engen, D. J. Am. Chem. Soc., 1989, 111, 6881-6882; Briner, K.; Vasella, A, Helv. Chim. Acta 1989, 72, 1371-1382; Kunz, H.; Wernig, P.; Schultz, M. Synlett 1990, 631-632; López, J. C; Fraser-Reid, B. J. Chem. Soc., Chem. Commun., 1991, 159-161; Barressi, F.; Hindsgaul, O. J. Am. Chem. Soc., 1991, 113, 9376-9377; Stork, G.; Kim, G. J. Am. Chem. Soc., 1992, 114, 1087-1088; Bols, M. Tetrahedron 1993, 49, 10049-10060; Ito, Y.; Ogawa, T. Angew. Chem., Int. Ed. Eng., 1994, 33, 1765-1767; Kondo, H.; Aoki, S.; Ichikawa, Y.; Halcomb, R. L.; Ritzen, H.; Wong, C.-H. J. Org. Chem., 1994, 59, 864-877;
17. For recent methods of chemical glycosylation: Mootoo, D. R.; Konradsson, P.; Udodong, U.; Fraser-Reid, B. J. Am. Chem. Soc., 1988, 110, 5583-5584; Kirchner, E.; Thiem, F.; Dernick, R.; Heukeshoven, J.; Thiem, J. J. Carbohydr. Chem., 1988, 7, 453-486; Nicolaou, K. C.; Caufield, T.; Kataoka, H.; Kumazawa, P. J. Am. Chem. Soc., 1988, 110, 7910-7912; 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; Friesen, R. W.; Danishefsky, S. J. Am. Chem. Soc., 1989, 111, 6656-6660; Halcomb, R. L.; Danishefsky, S. J. Am. Chem. Soc., 1989, 111, 6661-6666; Kahne, D.; Walker, S.; Cheng, Y.; van Engen, D. J. Am. Chem. Soc., 1989, 111, 6881-6882; Briner, K.; Vasella, A, Helv. Chim. Acta 1989, 72, 1371-1382; Kunz, H.; Wernig, P.; Schultz, M. Synlett 1990, 631-632; López, J. C; Fraser-Reid, B. J. Chem. Soc., Chem. Commun., 1991, 159-161; Barressi, F.; Hindsgaul, O. J. Am. Chem. Soc., 1991, 113, 9376-9377; Stork, G.; Kim, G. J. Am. Chem. Soc., 1992, 114, 1087-1088; Bols, M. Tetrahedron 1993, 49, 10049-10060; Ito, Y.; Ogawa, T. Angew. Chem., Int. Ed. Eng., 1994, 33, 1765-1767; Kondo, H.; Aoki, S.; Ichikawa, Y.; Halcomb, R. L.; Ritzen, H.; Wong, C.-H. J. Org. Chem., 1994, 59, 864-877;
18. For recent methods of chemical glycosylation: Mootoo, D. R.; Konradsson, P.; Udodong, U.; Fraser-Reid, B. J. Am. Chem. Soc., 1988, 110, 5583-5584; Kirchner, E.; Thiem, F.; Dernick, R.; Heukeshoven, J.; Thiem, J. J. Carbohydr. Chem., 1988, 7, 453-486; Nicolaou, K. C.; Caufield, T.; Kataoka, H.; Kumazawa, P. J. Am. Chem. Soc., 1988, 110, 7910-7912; 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; Friesen, R. W.; Danishefsky, S. J. Am. Chem. Soc., 1989, 111, 6656-6660; Halcomb, R. L.; Danishefsky, S. J. Am. Chem. Soc., 1989, 111, 6661-6666; Kahne, D.; Walker, S.; Cheng, Y.; van Engen, D. J. Am. Chem. Soc., 1989, 111, 6881-6882; Briner, K.; Vasella, A, Helv. Chim. Acta 1989, 72, 1371-1382; Kunz, H.; Wernig, P.; Schultz, M. Synlett 1990, 631-632; López, J. C; Fraser-Reid, B. J. Chem. Soc., Chem. Commun., 1991, 159-161; Barressi, F.; Hindsgaul, O. J. Am. Chem. Soc., 1991, 113, 9376-9377; Stork, G.; Kim, G. J. Am. Chem. Soc., 1992, 114, 1087-1088; Bols, M. Tetrahedron 1993, 49, 10049-10060; Ito, Y.; Ogawa, T. Angew. Chem., Int. Ed. Eng., 1994, 33, 1765-1767; Kondo, H.; Aoki, S.; Ichikawa, Y.; Halcomb, R. L.; Ritzen, H.; Wong, C.-H. J. Org. Chem., 1994, 59, 864-877;
19. For recent methods of chemical glycosylation: Mootoo, D. R.; Konradsson, P.; Udodong, U.; Fraser-Reid, B. J. Am. Chem. Soc., 1988, 110, 5583-5584; Kirchner, E.; Thiem, F.; Dernick, R.; Heukeshoven, J.; Thiem, J. J. Carbohydr. Chem., 1988, 7, 453-486; Nicolaou, K. C.; Caufield, T.; Kataoka, H.; Kumazawa, P. J. Am. Chem. Soc., 1988, 110, 7910-7912; 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; Friesen, R. W.; Danishefsky, S. J. Am. Chem. Soc., 1989, 111, 6656-6660; Halcomb, R. L.; Danishefsky, S. J. Am. Chem. Soc., 1989, 111, 6661-6666; Kahne, D.; Walker, S.; Cheng, Y.; van Engen, D. J. Am. Chem. Soc., 1989, 111, 6881-6882; Briner, K.; Vasella, A, Helv. Chim. Acta 1989, 72, 1371-1382; Kunz, H.; Wernig, P.; Schultz, M. Synlett 1990, 631-632; López, J. C; Fraser-Reid, B. J. Chem. Soc., Chem. Commun., 1991, 159-161; Barressi, F.; Hindsgaul, O. J. Am. Chem. Soc., 1991, 113, 9376-9377; Stork, G.; Kim, G. J. Am. Chem. Soc., 1992, 114, 1087-1088; Bols, M. Tetrahedron 1993, 49, 10049-10060; Ito, Y.; Ogawa, T. Angew. Chem., Int. Ed. Eng., 1994, 33, 1765-1767; Kondo, H.; Aoki, S.; Ichikawa, Y.; Halcomb, R. L.; Ritzen, H.; Wong, C.-H. J. Org. Chem., 1994, 59, 864-877;
20. For recent methods of chemical glycosylation: Mootoo, D. R.; Konradsson, P.; Udodong, U.; Fraser-Reid, B. J. Am. Chem. Soc., 1988, 110, 5583-5584; Kirchner, E.; Thiem, F.; Dernick, R.; Heukeshoven, J.; Thiem, J. J. Carbohydr. Chem., 1988, 7, 453-486; Nicolaou, K. C.; Caufield, T.; Kataoka, H.; Kumazawa, P. J. Am. Chem. Soc., 1988, 110, 7910-7912; 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; Friesen, R. W.; Danishefsky, S. J. Am. Chem. Soc., 1989, 111, 6656-6660; Halcomb, R. L.; Danishefsky, S. J. Am. Chem. Soc., 1989, 111, 6661-6666; Kahne, D.; Walker, S.; Cheng, Y.; van Engen, D. J. Am. Chem. Soc., 1989, 111, 6881-6882; Briner, K.; Vasella, A, Helv. Chim. Acta 1989, 72, 1371-1382; Kunz, H.; Wernig, P.; Schultz, M. Synlett 1990, 631-632; López, J. C; Fraser-Reid, B. J. Chem. Soc., Chem. Commun., 1991, 159-161; Barressi, F.; Hindsgaul, O. J. Am. Chem. Soc., 1991, 113, 9376-9377; Stork, G.; Kim, G. J. Am. Chem. Soc., 1992, 114, 1087-1088; Bols, M. Tetrahedron 1993, 49, 10049-10060; Ito, Y.; Ogawa, T. Angew. Chem., Int. Ed. Eng., 1994, 33, 1765-1767; Kondo, H.; Aoki, S.; Ichikawa, Y.; Halcomb, R. L.; Ritzen, H.; Wong, C.-H. J. Org. Chem., 1994, 59, 864-877;
21. For recent methods of chemical glycosylation: Mootoo, D. R.; Konradsson, P.; Udodong, U.; Fraser-Reid, B. J. Am. Chem. Soc., 1988, 110, 5583-5584; Kirchner, E.; Thiem, F.; Dernick, R.; Heukeshoven, J.; Thiem, J. J. Carbohydr. Chem., 1988, 7, 453-486; Nicolaou, K. C.; Caufield, T.; Kataoka, H.; Kumazawa, P. J. Am. Chem. Soc., 1988, 110, 7910-7912; 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; Friesen, R. W.; Danishefsky, S. J. Am. Chem. Soc., 1989, 111, 6656-6660; Halcomb, R. L.; Danishefsky, S. J. Am. Chem. Soc., 1989, 111, 6661-6666; Kahne, D.; Walker, S.; Cheng, Y.; van Engen, D. J. Am. Chem. Soc., 1989, 111, 6881-6882; Briner, K.; Vasella, A, Helv. Chim. Acta 1989, 72, 1371-1382; Kunz, H.; Wernig, P.; Schultz, M. Synlett 1990, 631-632; López, J. C; Fraser-Reid, B. J. Chem. Soc., Chem. Commun., 1991, 159-161; Barressi, F.; Hindsgaul, O. J. Am. Chem. Soc., 1991, 113, 9376-9377; Stork, G.; Kim, G. J. Am. Chem. Soc., 1992, 114, 1087-1088; Bols, M. Tetrahedron 1993, 49, 10049-10060; Ito, Y.; Ogawa, T. Angew. Chem., Int. Ed. Eng., 1994, 33, 1765-1767; Kondo, H.; Aoki, S.; Ichikawa, Y.; Halcomb, R. L.; Ritzen, H.; Wong, C.-H. J. Org. Chem., 1994, 59, 864-877;
22. For recent methods of chemical glycosylation: Mootoo, D. R.; Konradsson, P.; Udodong, U.; Fraser-Reid, B. J. Am. Chem. Soc., 1988, 110, 5583-5584; Kirchner, E.; Thiem, F.; Dernick, R.; Heukeshoven, J.; Thiem, J. J. Carbohydr. Chem., 1988, 7, 453-486; Nicolaou, K. C.; Caufield, T.; Kataoka, H.; Kumazawa, P. J. Am. Chem. Soc., 1988, 110, 7910-7912; 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; Friesen, R. W.; Danishefsky, S. J. Am. Chem. Soc., 1989, 111, 6656-6660; Halcomb, R. L.; Danishefsky, S. J. Am. Chem. Soc., 1989, 111, 6661-6666; Kahne, D.; Walker, S.; Cheng, Y.; van Engen, D. J. Am. Chem. Soc., 1989, 111, 6881-6882; Briner, K.; Vasella, A, Helv. Chim. Acta 1989, 72, 1371-1382; Kunz, H.; Wernig, P.; Schultz, M. Synlett 1990, 631-632; López, J. C; Fraser-Reid, B. J. Chem. Soc., Chem. Commun., 1991, 159-161; Barressi, F.; Hindsgaul, O. J. Am. Chem. Soc., 1991, 113, 9376-9377; Stork, G.; Kim, G. J. Am. Chem. Soc., 1992, 114, 1087-1088; Bols, M. Tetrahedron 1993, 49, 10049-10060; Ito, Y.; Ogawa, T. Angew. Chem., Int. Ed. Eng., 1994, 33, 1765-1767; Kondo, H.; Aoki, S.; Ichikawa, Y.; Halcomb, R. L.; Ritzen, H.; Wong, C.-H. J. Org. Chem., 1994, 59, 864-877;
23. For recent methods of chemical glycosylation: Mootoo, D. R.; Konradsson, P.; Udodong, U.; Fraser-Reid, B. J. Am. Chem. Soc., 1988, 110, 5583-5584; Kirchner, E.; Thiem, F.; Dernick, R.; Heukeshoven, J.; Thiem, J. J. Carbohydr. Chem., 1988, 7, 453-486; Nicolaou, K. C.; Caufield, T.; Kataoka, H.; Kumazawa, P. J. Am. Chem. Soc., 1988, 110, 7910-7912; 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; Friesen, R. W.; Danishefsky, S. J. Am. Chem. Soc., 1989, 111, 6656-6660; Halcomb, R. L.; Danishefsky, S. J. Am. Chem. Soc., 1989, 111, 6661-6666; Kahne, D.; Walker, S.; Cheng, Y.; van Engen, D. J. Am. Chem. Soc., 1989, 111, 6881-6882; Briner, K.; Vasella, A, Helv. Chim. Acta 1989, 72, 1371-1382; Kunz, H.; Wernig, P.; Schultz, M. Synlett 1990, 631-632; López, J. C; Fraser-Reid, B. J. Chem. Soc., Chem. Commun., 1991, 159-161; Barressi, F.; Hindsgaul, O. J. Am. Chem. Soc., 1991, 113, 9376-9377; Stork, G.; Kim, G. J. Am. Chem. Soc., 1992, 114, 1087-1088; Bols, M. Tetrahedron 1993, 49, 10049-10060; Ito, Y.; Ogawa, T. Angew. Chem., Int. Ed. Eng., 1994, 33, 1765-1767; Kondo, H.; Aoki, S.; Ichikawa, Y.; Halcomb, R. L.; Ritzen, H.; Wong, C.-H. J. Org. Chem., 1994, 59, 864-877;
24. For recent methods of chemical glycosylation: Mootoo, D. R.; Konradsson, P.; Udodong, U.; Fraser-Reid, B. J. Am. Chem. Soc., 1988, 110, 5583-5584; Kirchner, E.; Thiem, F.; Dernick, R.; Heukeshoven, J.; Thiem, J. J. Carbohydr. Chem., 1988, 7, 453-486; Nicolaou, K. C.; Caufield, T.; Kataoka, H.; Kumazawa, P. J. Am. Chem. Soc., 1988, 110, 7910-7912; 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; Friesen, R. W.; Danishefsky, S. J. Am. Chem. Soc., 1989, 111, 6656-6660; Halcomb, R. L.; Danishefsky, S. J. Am. Chem. Soc., 1989, 111, 6661-6666; Kahne, D.; Walker, S.; Cheng, Y.; van Engen, D. J. Am. Chem. Soc., 1989, 111, 6881-6882; Briner, K.; Vasella, A, Helv. Chim. Acta 1989, 72, 1371-1382; Kunz, H.; Wernig, P.; Schultz, M. Synlett 1990, 631-632; López, J. C; Fraser-Reid, B. J. Chem. Soc., Chem. Commun., 1991, 159-161; Barressi, F.; Hindsgaul, O. J. Am. Chem. Soc., 1991, 113, 9376-9377; Stork, G.; Kim, G. J. Am. Chem. Soc., 1992, 114, 1087-1088; Bols, M. Tetrahedron 1993, 49, 10049-10060; Ito, Y.; Ogawa, T. Angew. Chem., Int. Ed. Eng., 1994, 33, 1765-1767; Kondo, H.; Aoki, S.; Ichikawa, Y.; Halcomb, R. L.; Ritzen, H.; Wong, C.-H. J. Org. Chem., 1994, 59, 864-877;
25. Lopez, J. C.; Gómez, A. M.; Valverde, S.; Fraser-Reid, B. J. Org. Chem., 1995, 60, 3851-3858.
26. Valverde, S.; Gómez, A. M.; Hernández, A.; Herradón, B.; López, J. C. J. Chem. Soc., Chem. Commun., 1995, 2005-2006.
27. For a recent related approach: Ziegler, T.; Lau, R. Tetrahedron Lett., 1995, 36, 1417-1420.
28. All new compounds were purified by silica-gel column chromatography and were fully characterized by spectroscopic and analytical means.
29. The adducts reported in this paper were prepared in a regioselective manner from the corresponding monosaccharides by means of dibutylstannylidene acetal chemistry under microwave irradiation and details of these transformations will be reported elsewhere.
30. Konradsson, P.; Mootoo, D. R.; McDevitt, R. E.; Fraser-Reid, B. J. Chem. Soc., Chem. Commun., 1990, 270-272; Veeneman, G. H.; van Leeuwen, S. H.; Zuurmond, H.; van Boom, J. H. J. Carbohydr. Chem., 1990, 9, 783-796.
31. Konradsson, P.; Mootoo, D. R.; McDevitt, R. E.; Fraser-Reid, B. J. Chem. Soc., Chem. Commun., 1990, 270-272; Veeneman, G. H.; van Leeuwen, S. H.; Zuurmond, H.; van Boom, J. H. J. Carbohydr. Chem., 1990, 9, 783-796.
32. Birberg, W.; Lönn, H. Tetrahedron Lett., 1991, 32, 7453-7456.