Per-O-Trimethylsilyl-α-L-Fucopyranosyl Iodide: A Novel Glycosylating Agent for Terminal α-L-Fucosylation

Synlett

Volumn 1996, Issue 6, 1996, Pages 499-501

  Uchiyama, Taketo ^a   Hindsgaul, Ole ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 1542707090     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5491     Document Type: Article

References (17)

1. For the most recent review on oligosaccharide synthesis see: Boons, G.-J. Tetrahedron 1996, 52, 1095. For an ongoing review of the literature of oligosaccharide synthesis, currently listing over 700 glycosidic linkages that have been chemically synthesized beginning in 1994, see: Barresi, F.; Hindsgaul, O. J. Carbohydr. Chem. 1995, 14, 1043; or view it on the internet at http://glyco2.chem.ualberta.ca/GROUP/UAGBG.html
2. For the most recent review on oligosaccharide synthesis see: Boons, G.-J. Tetrahedron 1996, 52, 1095. For an ongoing review of the literature of oligosaccharide synthesis, currently listing over 700 glycosidic linkages that have been chemically synthesized beginning in 1994, see: Barresi, F.; Hindsgaul, O. J. Carbohydr. Chem. 1995, 14, 1043; or view it on the internet at http://glyco2.chem.ualberta.ca/GROUP/UAGBG.html
3. a) Kronzer, F.J.; Scherch, C. Carbohydr. Res. 1974, 34, 71.
4. b) Thiem, J.; Meyer, B. Chem. Ber. 1980, 113, 3075.
5. c) Ernst, B.; Winkler, T. Tetrahedron Lett. 1989, 30, 3081.
6. Varki, A. Glycobiology 1993, 3, 97.
7. 3) δ 95.54, 76.05, 70.64, 69.61, 66.63, 16.73, 0.67, 0.43, 0.29, 0.14
8. 3 × 3)
9. 3) δ 4.89 (br s, H-1α), 4.23 (d, J = 7.5 Hz, H-1β), 1.27 (d, J = 6.5 Hz, H-6 for β), 1.18 (d, J = 6.6 Hz, H-6 for α)
10. 3OD = 10:1).
11. For natural glycopeptide structures containing α-Fuc-Ser, see: a) Buko, A.M.; Kentzer, E.J.; Petros, A.; Menon, G.; Zuiderweg, E.R.P.; Sarin, V.K. Proc. Natl. Acad. Sci. USA 1991, 88, 3992. b) Bjoern, S.; Foster, D.C.; Thim, L.; Wiberg, F.C.; Christensen, M.; Komiyama, Y.; Pederson, A.H.; Kisil, W. J. Biol. Chem. 1991, 266, 1105. c) Harris, R.J.; Ling, V.T.; Spellman, M.W. J. Biol. Chem. 1992, 267, 5102. d) Nakakura, N.; Hietter, H.; Van Dorsselaer, A.; Lunn, B. Eur. J. Biochem. 1992, 204, 147.
12. For natural glycopeptide structures containing α-Fuc-Ser, see: a) Buko, A.M.; Kentzer, E.J.; Petros, A.; Menon, G.; Zuiderweg, E.R.P.; Sarin, V.K. Proc. Natl. Acad. Sci. USA 1991, 88, 3992. b) Bjoern, S.; Foster, D.C.; Thim, L.; Wiberg, F.C.; Christensen, M.; Komiyama, Y.; Pederson, A.H.; Kisil, W. J. Biol. Chem. 1991, 266, 1105. c) Harris, R.J.; Ling, V.T.; Spellman, M.W. J. Biol. Chem. 1992, 267, 5102. d) Nakakura, N.; Hietter, H.; Van Dorsselaer, A.; Lunn, B. Eur. J. Biochem. 1992, 204, 147.
13. For natural glycopeptide structures containing α-Fuc-Ser, see: a) Buko, A.M.; Kentzer, E.J.; Petros, A.; Menon, G.; Zuiderweg, E.R.P.; Sarin, V.K. Proc. Natl. Acad. Sci. USA 1991, 88, 3992. b) Bjoern, S.; Foster, D.C.; Thim, L.; Wiberg, F.C.; Christensen, M.; Komiyama, Y.; Pederson, A.H.; Kisil, W. J. Biol. Chem. 1991, 266, 1105. c) Harris, R.J.; Ling, V.T.; Spellman, M.W. J. Biol. Chem. 1992, 267, 5102. d) Nakakura, N.; Hietter, H.; Van Dorsselaer, A.; Lunn, B. Eur. J. Biochem. 1992, 204, 147.
14. For natural glycopeptide structures containing α-Fuc-Ser, see: a) Buko, A.M.; Kentzer, E.J.; Petros, A.; Menon, G.; Zuiderweg, E.R.P.; Sarin, V.K. Proc. Natl. Acad. Sci. USA 1991, 88, 3992. b) Bjoern, S.; Foster, D.C.; Thim, L.; Wiberg, F.C.; Christensen, M.; Komiyama, Y.; Pederson, A.H.; Kisil, W. J. Biol. Chem. 1991, 266, 1105. c) Harris, R.J.; Ling, V.T.; Spellman, M.W. J. Biol. Chem. 1992, 267, 5102. d) Nakakura, N.; Hietter, H.; Van Dorsselaer, A.; Lunn, B. Eur. J. Biochem. 1992, 204, 147.
15. For syntheses of α-Fuc-Ser, see: e) Hietter, H.; Schultz, M.; Kunz, H. Synlett 1995, 12, 1219. f) Peter, S.; Lowary, T.; Hindsgaul, O.; Meldal, M.; Boch, K. J. Chem. Soc. Perkin Trans. I 1995, 3017.
16. For syntheses of α-Fuc-Ser, see: e) Hietter, H.; Schultz, M.; Kunz, H. Synlett 1995, 12, 1219. f) Peter, S.; Lowary, T.; Hindsgaul, O.; Meldal, M.; Boch, K. J. Chem. Soc. Perkin Trans. I 1995, 3017.
17. +