Repetitive Solid Phase Glycosylation on an Alkyl Thiol Polyme Leading to Sugar Oligomers Containing 1,2-trans- And 1,2-cis-Glycosidic Linkages

Journal of Organic Chemistry

Volumn 62, Issue 11, 1997, Pages 3650-3653

  Rademann, Jörg ^a   Schmidt, Richard R ^a  

^a UNIVERSITY OF KONSTANZ   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000932220     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970087f     Document Type: Article

References (35)

1. For reviews on glycosylation, see: (a) Paulsen, H. Angew. Chem. 1982, 94, 184; Angew. Chem. Int. Ed. Engl. 1982, 21, 155. (b) Schmidt, R. R. Angew. Chem. 1986, 98, 213; Angew. Chem. Int. Ed. Engl. 1986, 25, 212. (c) Schmidt, R. R. In Carbohydrates-Synthetic Methods and Applications in Medicinal Chemistry; Ogura, H., Hasegawa, A., Suami, T., Eds.; Tokyo, 1992; p 68. (d) Toshima, K.; Tatsuta, K. Chem. Rev. 1993, 93, 1503. (e) Ogawa, T. Chem. Soc. Rev. 1994, 397. (f) Barresi, F.; Hindsgaul, O. In Modern Synthetic Methods 1995; Ernst, B., Leumann, C., Eds.; Weinheim/Basel, 1995; p 283.
2. For reviews on glycosylation, see: (a) Paulsen, H. Angew. Chem. 1982, 94, 184; Angew. Chem. Int. Ed. Engl. 1982, 21, 155. (b) Schmidt, R. R. Angew. Chem. 1986, 98, 213; Angew. Chem. Int. Ed. Engl. 1986, 25, 212. (c) Schmidt, R. R. In Carbohydrates-Synthetic Methods and Applications in Medicinal Chemistry; Ogura, H., Hasegawa, A., Suami, T., Eds.; Tokyo, 1992; p 68. (d) Toshima, K.; Tatsuta, K. Chem. Rev. 1993, 93, 1503. (e) Ogawa, T. Chem. Soc. Rev. 1994, 397. (f) Barresi, F.; Hindsgaul, O. In Modern Synthetic Methods 1995; Ernst, B., Leumann, C., Eds.; Weinheim/Basel, 1995; p 283.
3. For reviews on glycosylation, see: (a) Paulsen, H. Angew. Chem. 1982, 94, 184; Angew. Chem. Int. Ed. Engl. 1982, 21, 155. (b) Schmidt, R. R. Angew. Chem. 1986, 98, 213; Angew. Chem. Int. Ed. Engl. 1986, 25, 212. (c) Schmidt, R. R. In Carbohydrates-Synthetic Methods and Applications in Medicinal Chemistry; Ogura, H., Hasegawa, A., Suami, T., Eds.; Tokyo, 1992; p 68. (d) Toshima, K.; Tatsuta, K. Chem. Rev. 1993, 93, 1503. (e) Ogawa, T. Chem. Soc. Rev. 1994, 397. (f) Barresi, F.; Hindsgaul, O. In Modern Synthetic Methods 1995; Ernst, B., Leumann, C., Eds.; Weinheim/Basel, 1995; p 283.
4. For reviews on glycosylation, see: (a) Paulsen, H. Angew. Chem. 1982, 94, 184; Angew. Chem. Int. Ed. Engl. 1982, 21, 155. (b) Schmidt, R. R. Angew. Chem. 1986, 98, 213; Angew. Chem. Int. Ed. Engl. 1986, 25, 212. (c) Schmidt, R. R. In Carbohydrates-Synthetic Methods and Applications in Medicinal Chemistry; Ogura, H., Hasegawa, A., Suami, T., Eds.; Tokyo, 1992; p 68. (d) Toshima, K.; Tatsuta, K. Chem. Rev. 1993, 93, 1503. (e) Ogawa, T. Chem. Soc. Rev. 1994, 397. (f) Barresi, F.; Hindsgaul, O. In Modern Synthetic Methods 1995; Ernst, B., Leumann, C., Eds.; Weinheim/Basel, 1995; p 283.
5. For reviews on glycosylation, see: (a) Paulsen, H. Angew. Chem. 1982, 94, 184; Angew. Chem. Int. Ed. Engl. 1982, 21, 155. (b) Schmidt, R. R. Angew. Chem. 1986, 98, 213; Angew. Chem. Int. Ed. Engl. 1986, 25, 212. (c) Schmidt, R. R. In Carbohydrates-Synthetic Methods and Applications in Medicinal Chemistry; Ogura, H., Hasegawa, A., Suami, T., Eds.; Tokyo, 1992; p 68. (d) Toshima, K.; Tatsuta, K. Chem. Rev. 1993, 93, 1503. (e) Ogawa, T. Chem. Soc. Rev. 1994, 397. (f) Barresi, F.; Hindsgaul, O. In Modern Synthetic Methods 1995; Ernst, B., Leumann, C., Eds.; Weinheim/Basel, 1995; p 283.
6. For reviews on glycosylation, see: (a) Paulsen, H. Angew. Chem. 1982, 94, 184; Angew. Chem. Int. Ed. Engl. 1982, 21, 155. (b) Schmidt, R. R. Angew. Chem. 1986, 98, 213; Angew. Chem. Int. Ed. Engl. 1986, 25, 212. (c) Schmidt, R. R. In Carbohydrates-Synthetic Methods and Applications in Medicinal Chemistry; Ogura, H., Hasegawa, A., Suami, T., Eds.; Tokyo, 1992; p 68. (d) Toshima, K.; Tatsuta, K. Chem. Rev. 1993, 93, 1503. (e) Ogawa, T. Chem. Soc. Rev. 1994, 397. (f) Barresi, F.; Hindsgaul, O. In Modern Synthetic Methods 1995; Ernst, B., Leumann, C., Eds.; Weinheim/Basel, 1995; p 283.
7. For reviews on glycosylation, see: (a) Paulsen, H. Angew. Chem. 1982, 94, 184; Angew. Chem. Int. Ed. Engl. 1982, 21, 155. (b) Schmidt, R. R. Angew. Chem. 1986, 98, 213; Angew. Chem. Int. Ed. Engl. 1986, 25, 212. (c) Schmidt, R. R. In Carbohydrates-Synthetic Methods and Applications in Medicinal Chemistry; Ogura, H., Hasegawa, A., Suami, T., Eds.; Tokyo, 1992; p 68. (d) Toshima, K.; Tatsuta, K. Chem. Rev. 1993, 93, 1503. (e) Ogawa, T. Chem. Soc. Rev. 1994, 397. (f) Barresi, F.; Hindsgaul, O. In Modern Synthetic Methods 1995; Ernst, B., Leumann, C., Eds.; Weinheim/Basel, 1995; p 283.
8. For reviews on glycosylation, see: (a) Paulsen, H. Angew. Chem. 1982, 94, 184; Angew. Chem. Int. Ed. Engl. 1982, 21, 155. (b) Schmidt, R. R. Angew. Chem. 1986, 98, 213; Angew. Chem. Int. Ed. Engl. 1986, 25, 212. (c) Schmidt, R. R. In Carbohydrates-Synthetic Methods and Applications in Medicinal Chemistry; Ogura, H., Hasegawa, A., Suami, T., Eds.; Tokyo, 1992; p 68. (d) Toshima, K.; Tatsuta, K. Chem. Rev. 1993, 93, 1503. (e) Ogawa, T. Chem. Soc. Rev. 1994, 397. (f) Barresi, F.; Hindsgaul, O. In Modern Synthetic Methods 1995; Ernst, B., Leumann, C., Eds.; Weinheim/Basel, 1995; p 283.
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18. For more recent chemical glycosylations on the solid phase: (a) Danishefsky, S. J.; McClure, K. F.; Randolph, J. T.; Ruggeri, R. B. Science 1993, 260, 1307. (c) Van, L.; Taylor, C. M.; Goodnow, R.; Kahne, D. J. Am. Chem. Soc. 1994, 116, 6953. Liang, R.; Yan, L.; Loebach, J.; Ge, M.; Uozumi, Y.; Sekanina, K.; Horan, N.; Gildersleeve, J.; Thompson, C.; Smith, A.; Biswas, K.; Still, W. C.; Kahne, D. Science, 1996, 274, 1520. (c) Hunt, J. A.; Roush, W. R. J. Am. Chem. Soc. 1996, 118, 9998. (d) Andinolfi, M.; Barone, G.; De Napoli, L.; Iadonisi, A.; Piccialli, G. Tetrahedron Lett. 1996, 37, 5007. (e) For enzymatic glycosations on the solid phase, see: Schuster, M.; Wang, P.; Paulson, J. C.; Wong, C.-H. J. Am. Chem. Soc. 1994, 116, 1135. (f) For oligosaccharide synthesis on a soluble polymer, see: ref 12 a,b.
19. For more recent chemical glycosylations on the solid phase: (a) Danishefsky, S. J.; McClure, K. F.; Randolph, J. T.; Ruggeri, R. B. Science 1993, 260, 1307. (c) Van, L.; Taylor, C. M.; Goodnow, R.; Kahne, D. J. Am. Chem. Soc. 1994, 116, 6953. Liang, R.; Yan, L.; Loebach, J.; Ge, M.; Uozumi, Y.; Sekanina, K.; Horan, N.; Gildersleeve, J.; Thompson, C.; Smith, A.; Biswas, K.; Still, W. C.; Kahne, D. Science, 1996, 274, 1520. (c) Hunt, J. A.; Roush, W. R. J. Am. Chem. Soc. 1996, 118, 9998. (d) Andinolfi, M.; Barone, G.; De Napoli, L.; Iadonisi, A.; Piccialli, G. Tetrahedron Lett. 1996, 37, 5007. (e) For enzymatic glycosations on the solid phase, see: Schuster, M.; Wang, P.; Paulson, J. C.; Wong, C.-H. J. Am. Chem. Soc. 1994, 116, 1135. (f) For oligosaccharide synthesis on a soluble polymer, see: ref 12 a,b.
20. For more recent chemical glycosylations on the solid phase: (a) Danishefsky, S. J.; McClure, K. F.; Randolph, J. T.; Ruggeri, R. B. Science 1993, 260, 1307. (c) Van, L.; Taylor, C. M.; Goodnow, R.; Kahne, D. J. Am. Chem. Soc. 1994, 116, 6953. Liang, R.; Yan, L.; Loebach, J.; Ge, M.; Uozumi, Y.; Sekanina, K.; Horan, N.; Gildersleeve, J.; Thompson, C.; Smith, A.; Biswas, K.; Still, W. C.; Kahne, D. Science, 1996, 274, 1520. (c) Hunt, J. A.; Roush, W. R. J. Am. Chem. Soc. 1996, 118, 9998. (d) Andinolfi, M.; Barone, G.; De Napoli, L.; Iadonisi, A.; Piccialli, G. Tetrahedron Lett. 1996, 37, 5007. (e) For enzymatic glycosations on the solid phase, see: Schuster, M.; Wang, P.; Paulson, J. C.; Wong, C.-H. J. Am. Chem. Soc. 1994, 116, 1135. (f) For oligosaccharide synthesis on a soluble polymer, see: ref 12 a,b.
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22. For more recent chemical glycosylations on the solid phase: (a) Danishefsky, S. J.; McClure, K. F.; Randolph, J. T.; Ruggeri, R. B. Science 1993, 260, 1307. (c) Van, L.; Taylor, C. M.; Goodnow, R.; Kahne, D. J. Am. Chem. Soc. 1994, 116, 6953. Liang, R.; Yan, L.; Loebach, J.; Ge, M.; Uozumi, Y.; Sekanina, K.; Horan, N.; Gildersleeve, J.; Thompson, C.; Smith, A.; Biswas, K.; Still, W. C.; Kahne, D. Science, 1996, 274, 1520. (c) Hunt, J. A.; Roush, W. R. J. Am. Chem. Soc. 1996, 118, 9998. (d) Andinolfi, M.; Barone, G.; De Napoli, L.; Iadonisi, A.; Piccialli, G. Tetrahedron Lett. 1996, 37, 5007. (e) For enzymatic glycosations on the solid phase, see: Schuster, M.; Wang, P.; Paulson, J. C.; Wong, C.-H. J. Am. Chem. Soc. 1994, 116, 1135. (f) For oligosaccharide synthesis on a soluble polymer, see: ref 12 a,b.
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