Fluorinated carbohydrates. Some new aspects in synthesis and application

Current Organic Chemistry

Volumn 3, Issue 3, 1999, Pages 287-307

  Dax, K ^a   Albert, M ^a   Ortner, J ^a   Paul, B J ^a  

^a GRAZ UNIVERSITY OF TECHNOLOGY   (Austria)

Author keywords

[No Author keywords available]

Indexed keywords

2 DEOXY 2 FLUOROALDOSE DERIVATIVE; CARBOHYDRATE; HYDROXYL GROUP; OLIGOSACCHARIDE; UNCLASSIFIED DRUG;

ARTICLE; CARBOHYDRATE ANALYSIS; CHEMICAL REACTION; ENZYME ACTIVITY; FLUORINATION; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032947968     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (124)

1. O. Hindsgaul, I. Lindh, N. J. Dovichi, J.-Y. Zhao, S. C. Crawley, S. Gosselin and M. M. Palcic: "Synthetic Toys for Glycobiology" in "Complex Carbohydrates in Drug Research", eds. K. Bock and H. Clausen, Munksgaard: Copenhagen, 1994, pp. 104-117.
2. W. D. Hitz in "Fluorinated Carbohydrates", ed. N. F. Taylor, ACS Symposium Ser. 1988, 374, pp. 138-155; S. J. Gatley, J. E. Holden, T. R. DeGrado, C. K. Ng, J. R. Halama and R. A. Koeppe, ACS Symposium Ser. 1988, 374, 156-175; N. F. Taylor, D. Sbrissa, S. T. Squire, T. D'Amore and J. M. McIntosh, ACS Symposium Ser. 1988, 374, pp. 109-137.
3. W. D. Hitz in "Fluorinated Carbohydrates", ed. N. F. Taylor, ACS Symposium Ser. 1988, 374, pp. 138-155; S. J. Gatley, J. E. Holden, T. R. DeGrado, C. K. Ng, J. R. Halama and R. A. Koeppe, ACS Symposium Ser. 1988, 374, 156-175; N. F. Taylor, D. Sbrissa, S. T. Squire, T. D'Amore and J. M. McIntosh, ACS Symposium Ser. 1988, 374, pp. 109-137.
4. W. D. Hitz in "Fluorinated Carbohydrates", ed. N. F. Taylor, ACS Symposium Ser. 1988, 374, pp. 138-155; S. J. Gatley, J. E. Holden, T. R. DeGrado, C. K. Ng, J. R. Halama and R. A. Koeppe, ACS Symposium Ser. 1988, 374, 156-175; N. F. Taylor, D. Sbrissa, S. T. Squire, T. D'Amore and J. M. McIntosh, ACS Symposium Ser. 1988, 374, pp. 109-137.
5. C. P. J. Glaudemans, P. Kovac, E. M. Nashed, E. A. Padlan and S. R. Arepalli in "Synthetic Oligosaccharides", ed. P. Kovac, ACS Symposium Ser. 1994, 560, pp. 157-183; S. G. Withers, I. P. Street and M. D. Percival in "Fluorinated Carbohydrates", ed. N. F. Taylor, ACS Symposium Ser. 1988, 374, pp. 59-77.
6. C. P. J. Glaudemans, P. Kovac, E. M. Nashed, E. A. Padlan and S. R. Arepalli in "Synthetic Oligosaccharides", ed. P. Kovac, ACS Symposium Ser. 1994, 560, pp. 157-183; S. G. Withers, I. P. Street and M. D. Percival in "Fluorinated Carbohydrates", ed. N. F. Taylor, ACS Symposium Ser. 1988, 374, pp. 59-77.
7. J. J. Fox, K. A. Watanabe, T. C. Chou, R. F. Schinazi, K. F. Soike, I. Fourel, G. Hantz and C. Trepo in "Fluorinated Carbohydrates", ed. N. F. Taylor, ACS Symposium Ser. 1988, 374, pp. 176-190; D. E. Bergstrom and D. J. Swartling in "Fluorine-Containing Molecules", eds. J. F. Liebman, A. Greenberg and W. R. Dolbier, Jr., VCh: Weinheim, 1988, pp. 259-308; P. Herdewijn, A. Van Aerschot and L. Kerremans, Nucleos. Nucleot., 1989, 8, 65-96.
8. J. J. Fox, K. A. Watanabe, T. C. Chou, R. F. Schinazi, K. F. Soike, I. Fourel, G. Hantz and C. Trepo in "Fluorinated Carbohydrates", ed. N. F. Taylor, ACS Symposium Ser. 1988, 374, pp. 176-190; D. E. Bergstrom and D. J. Swartling in "Fluorine-Containing Molecules", eds. J. F. Liebman, A. Greenberg and W. R. Dolbier, Jr., VCh: Weinheim, 1988, pp. 259-308; P. Herdewijn, A. Van Aerschot and L. Kerremans, Nucleos. Nucleot., 1989, 8, 65-96.
9. J. J. Fox, K. A. Watanabe, T. C. Chou, R. F. Schinazi, K. F. Soike, I. Fourel, G. Hantz and C. Trepo in "Fluorinated Carbohydrates", ed. N. F. Taylor, ACS Symposium Ser. 1988, 374, pp. 176-190; D. E. Bergstrom and D. J. Swartling in "Fluorine-Containing Molecules", eds. J. F. Liebman, A. Greenberg and W. R. Dolbier, Jr., VCh: Weinheim, 1988, pp. 259-308; P. Herdewijn, A. Van Aerschot and L. Kerremans, Nucleos. Nucleot., 1989, 8, 65-96.
10. A. A. Penglis, Adv. Carbohydr. Chem. Biochem., 1981, 38, 195-285; P. J. Card, J. Carbohydr. Chem., 1985, 4, 451-487; J. T. Welch, Tetrahedron, 1987, 43, 3123-3197; K. Toshima and T. Tatsuta, Chem. Rev., 1993, 93, 1503-1531.
11. A. A. Penglis, Adv. Carbohydr. Chem. Biochem., 1981, 38, 195-285; P. J. Card, J. Carbohydr. Chem., 1985, 4, 451-487; J. T. Welch, Tetrahedron, 1987, 43, 3123-3197; K. Toshima and T. Tatsuta, Chem. Rev., 1993, 93, 1503-1531.
12. A. A. Penglis, Adv. Carbohydr. Chem. Biochem., 1981, 38, 195-285; P. J. Card, J. Carbohydr. Chem., 1985, 4, 451-487; J. T. Welch, Tetrahedron, 1987, 43, 3123-3197; K. Toshima and T. Tatsuta, Chem. Rev., 1993, 93, 1503-1531.
13. A. A. Penglis, Adv. Carbohydr. Chem. Biochem., 1981, 38, 195-285; P. J. Card, J. Carbohydr. Chem., 1985, 4, 451-487; J. T. Welch, Tetrahedron, 1987, 43, 3123-3197; K. Toshima and T. Tatsuta, Chem. Rev., 1993, 93, 1503-1531.
14. R. Csuk and B. I. Glänzer, Adv. Carbohydr. Chem. Biochem., 1988, 46, 73-177.
15. T. Tsuchiya, Adv. Carbohydr. Chem. Biochem., 1990, 48, 91-277.
16. M. Shimizu, H. Togo and M. Yokoyama, Synthesis, 1998, 799-822.
17. K. C. Nicolaou and H. Ueno in "Preparative Carbohydrate Chemistry", ed. S. Hanessian, Marcel Dekker: New York-Basel-Hong Kong, 1997, pp. 313-338; O. Kanie and T. Ogawa in Med. Chem.: Today Tomorrow, Proc. AFMC Int. Med. Chem. Symp. 1995, ed. M. Yamazaki, Blackwell: Oxford, 1997, pp. 221-226 [CA 128: 140934u]; Z.-G. Wang, X.-F. Zhang, Y. Ito, Y. Nakahara and T. Ogawa, Carbohydr. Res., 1996, 295, 25-39; T. Nishimura and F. Nakatsubo, Carbohydr. Res., 1996, 294, 53-64; W. Bröder and H. Kunz, Bioorg. Med. Chem., 1997, 5, 1-19; G.-J. Boons, Tetrahedron, 1996, 52, 1095-1121; H. Paulsen, Angew. Chem., 1995, 107, 1562-1567.
18. K. C. Nicolaou and H. Ueno in "Preparative Carbohydrate Chemistry", ed. S. Hanessian, Marcel Dekker: New York-Basel-Hong Kong, 1997, pp. 313-338; O. Kanie and T. Ogawa in Med. Chem.: Today Tomorrow, Proc. AFMC Int. Med. Chem. Symp. 1995, ed. M. Yamazaki, Blackwell: Oxford, 1997, pp. 221-226 [CA 128: 140934u]; Z.-G. Wang, X.-F. Zhang, Y. Ito, Y. Nakahara and T. Ogawa, Carbohydr. Res., 1996, 295, 25-39; T. Nishimura and F. Nakatsubo, Carbohydr. Res., 1996, 294, 53-64; W. Bröder and H. Kunz, Bioorg. Med. Chem., 1997, 5, 1-19; G.-J. Boons, Tetrahedron, 1996, 52, 1095-1121; H. Paulsen, Angew. Chem., 1995, 107, 1562-1567.
19. K. C. Nicolaou and H. Ueno in "Preparative Carbohydrate Chemistry", ed. S. Hanessian, Marcel Dekker: New York-Basel-Hong Kong, 1997, pp. 313-338; O. Kanie and T. Ogawa in Med. Chem.: Today Tomorrow, Proc. AFMC Int. Med. Chem. Symp. 1995, ed. M. Yamazaki, Blackwell: Oxford, 1997, pp. 221-226 [CA 128: 140934u]; Z.-G. Wang, X.-F. Zhang, Y. Ito, Y. Nakahara and T. Ogawa, Carbohydr. Res., 1996, 295, 25-39; T. Nishimura and F. Nakatsubo, Carbohydr. Res., 1996, 294, 53-64; W. Bröder and H. Kunz, Bioorg. Med. Chem., 1997, 5, 1-19; G.-J. Boons, Tetrahedron, 1996, 52, 1095-1121; H. Paulsen, Angew. Chem., 1995, 107, 1562-1567.
20. K. C. Nicolaou and H. Ueno in "Preparative Carbohydrate Chemistry", ed. S. Hanessian, Marcel Dekker: New York-Basel-Hong Kong, 1997, pp. 313-338; O. Kanie and T. Ogawa in Med. Chem.: Today Tomorrow, Proc. AFMC Int. Med. Chem. Symp. 1995, ed. M. Yamazaki, Blackwell: Oxford, 1997, pp. 221-226 [CA 128: 140934u]; Z.-G. Wang, X.-F. Zhang, Y. Ito, Y. Nakahara and T. Ogawa, Carbohydr. Res., 1996, 295, 25-39; T. Nishimura and F. Nakatsubo, Carbohydr. Res., 1996, 294, 53-64; W. Bröder and H. Kunz, Bioorg. Med. Chem., 1997, 5, 1-19; G.-J. Boons, Tetrahedron, 1996, 52, 1095-1121; H. Paulsen, Angew. Chem., 1995, 107, 1562-1567.
21. K. C. Nicolaou and H. Ueno in "Preparative Carbohydrate Chemistry", ed. S. Hanessian, Marcel Dekker: New York-Basel-Hong Kong, 1997, pp. 313-338; O. Kanie and T. Ogawa in Med. Chem.: Today Tomorrow, Proc. AFMC Int. Med. Chem. Symp. 1995, ed. M. Yamazaki, Blackwell: Oxford, 1997, pp. 221-226 [CA 128: 140934u]; Z.-G. Wang, X.-F. Zhang, Y. Ito, Y. Nakahara and T. Ogawa, Carbohydr. Res., 1996, 295, 25-39; T. Nishimura and F. Nakatsubo, Carbohydr. Res., 1996, 294, 53-64; W. Bröder and H. Kunz, Bioorg. Med. Chem., 1997, 5, 1-19; G.-J. Boons, Tetrahedron, 1996, 52, 1095-1121; H. Paulsen, Angew. Chem., 1995, 107, 1562-1567.
22. K. C. Nicolaou and H. Ueno in "Preparative Carbohydrate Chemistry", ed. S. Hanessian, Marcel Dekker: New York-Basel-Hong Kong, 1997, pp. 313-338; O. Kanie and T. Ogawa in Med. Chem.: Today Tomorrow, Proc. AFMC Int. Med. Chem. Symp. 1995, ed. M. Yamazaki, Blackwell: Oxford, 1997, pp. 221-226 [CA 128: 140934u]; Z.-G. Wang, X.-F. Zhang, Y. Ito, Y. Nakahara and T. Ogawa, Carbohydr. Res., 1996, 295, 25-39; T. Nishimura and F. Nakatsubo, Carbohydr. Res., 1996, 294, 53-64; W. Bröder and H. Kunz, Bioorg. Med. Chem., 1997, 5, 1-19; G.-J. Boons, Tetrahedron, 1996, 52, 1095-1121; H. Paulsen, Angew. Chem., 1995, 107, 1562-1567.
23. K. C. Nicolaou and H. Ueno in "Preparative Carbohydrate Chemistry", ed. S. Hanessian, Marcel Dekker: New York-Basel-Hong Kong, 1997, pp. 313-338; O. Kanie and T. Ogawa in Med. Chem.: Today Tomorrow, Proc. AFMC Int. Med. Chem. Symp. 1995, ed. M. Yamazaki, Blackwell: Oxford, 1997, pp. 221-226 [CA 128: 140934u]; Z.-G. Wang, X.-F. Zhang, Y. Ito, Y. Nakahara and T. Ogawa, Carbohydr. Res., 1996, 295, 25-39; T. Nishimura and F. Nakatsubo, Carbohydr. Res., 1996, 294, 53-64; W. Bröder and H. Kunz, Bioorg. Med. Chem., 1997, 5, 1-19; G.-J. Boons, Tetrahedron, 1996, 52, 1095-1121; H. Paulsen, Angew. Chem., 1995, 107, 1562-1567.
24. I. Barrena, R. Echarri and S. Castillon, Synlett, 1996, 675-676.
25. Compare the "armed-disarmed" concept previously elaborated with 4-pentenyl and thioglycosides: B. Fraser-Reid, Z. Wu, U. Udodong and H. Ottosson, J. Org. Chem, 1990, 55, 6068-6070; G. H. Veeneman, S. H. van Leeuwen and J. H. van Boom, Tetrahedron Lett., 1990, 31, 1331-1334.
26. Compare the "armed-disarmed" concept previously elaborated with 4-pentenyl and thioglycosides: B. Fraser-Reid, Z. Wu, U. Udodong and H. Ottosson, J. Org. Chem, 1990, 55, 6068-6070; G. H. Veeneman, S. H. van Leeuwen and J. H. van Boom, Tetrahedron Lett., 1990, 31, 1331-1334.
27. L. Green, B. Hinzen, S. J. Ince, P. Langer, S. V. Ley and S. L. Warriner, Synlett, 1998, 440-442; M.-K. Cheung, N. L. Douglas, B. Hinzen, S. V. Ley and X. Pannecoucke, Synlett, 1997, 257-260.
28. L. Green, B. Hinzen, S. J. Ince, P. Langer, S. V. Ley and S. L. Warriner, Synlett, 1998, 440-442; M.-K. Cheung, N. L. Douglas, B. Hinzen, S. V. Ley and X. Pannecoucke, Synlett, 1997, 257-260.
29. N. L. Douglas, S. V. Ley, H. M. I. Osborn, D. R. Owen, H. W. M. Priepke and S. L. Warriner, Synlett, 1996, 793-795; J.-L. Montchamp, F. Tian, M. E. Hart and J. W. Frost, J. Org. Chem, 1996, 61, 3897-3899; U. Berens, D. Leckel and S. C. Oepen, J. Org. Chem., 1995, 60, 8204-8208.
30. N. L. Douglas, S. V. Ley, H. M. I. Osborn, D. R. Owen, H. W. M. Priepke and S. L. Warriner, Synlett, 1996, 793-795; J.-L. Montchamp, F. Tian, M. E. Hart and J. W. Frost, J. Org. Chem, 1996, 61, 3897-3899; U. Berens, D. Leckel and S. C. Oepen, J. Org. Chem., 1995, 60, 8204-8208.
31. N. L. Douglas, S. V. Ley, H. M. I. Osborn, D. R. Owen, H. W. M. Priepke and S. L. Warriner, Synlett, 1996, 793-795; J.-L. Montchamp, F. Tian, M. E. Hart and J. W. Frost, J. Org. Chem, 1996, 61, 3897-3899; U. Berens, D. Leckel and S. C. Oepen, J. Org. Chem., 1995, 60, 8204-8208.
32. W.-S. Kim, H. Sasai and M. Shibasaki, Tetrahedron Lett., 1996, 37, 7797-7800; see also: W.-S. Kim, S. Hosono, H. Sasai and M. Shibasaki, Tetrahedron Lett., 1995, 36, 4443-4446; S. Hosono, W.-S. Kim, H. Sasai and M. Shibasaki, J. Org. Chem, 1995, 60, 4-5.
33. W.-S. Kim, H. Sasai and M. Shibasaki, Tetrahedron Lett., 1996, 37, 7797-7800; see also: W.-S. Kim, S. Hosono, H. Sasai and M. Shibasaki, Tetrahedron Lett., 1995, 36, 4443-4446; S. Hosono, W.-S. Kim, H. Sasai and M. Shibasaki, J. Org. Chem, 1995, 60, 4-5.
34. W.-S. Kim, H. Sasai and M. Shibasaki, Tetrahedron Lett., 1996, 37, 7797-7800; see also: W.-S. Kim, S. Hosono, H. Sasai and M. Shibasaki, Tetrahedron Lett., 1995, 36, 4443-4446; S. Hosono, W.-S. Kim, H. Sasai and M. Shibasaki, J. Org. Chem, 1995, 60, 4-5.
35. K. Takeuchi and T. Mukaiyama, Chem. Lett., 1998, 555-556.
36. J. C. W. Chien, W.-M. Tsai and M. D. Rausch, J. Am. Chem. Soc., 1991, 113, 8570-8571.
37. A. Ogawa and D. P. Curran, J. Org. Chem., 1997, 62, 450-451.
38. H. Uchiro and T. Mukaiyama, Chem. Lett., 1997, 121-122.
39. For an overview on enzymatic transglycosylations see: K. G. I. Nilsson, Trends Biotechnol., 1988, 6, 256-264; R. Stiller and J. Thiem in "Jahrbuch der Biotechnologie", Karl Hanser: München, 1990, vol. 3, 114-120; K. G. I. Nilsson in "Enzymes in Carbohydrate Synthesis", eds. M. D. Bednarski and E. S. Simon, ACS Symposium Ser. 1991, 466, pp. 51-62; P. Stangier and J. Thiem , ACS Symposium Ser. 1991, 466, pp. 63-68; C.-H-Wong, R. L. Halcomb, Y. Ichikawa and T. Kajimoto, Angew. Chem., 1995, 107, 581-582; R. L. Halcomb in "Enzyme Catalysis in Organic Synthesis", eds. K. Drauz and H. Waldmann, VCh: Weinheim-New York-Basel-Cambridge-Tokyo, 1995, Vol. 1, pp. 303-306.
40. For an overview on enzymatic transglycosylations see: K. G. I. Nilsson, Trends Biotechnol., 1988, 6, 256-264; R. Stiller and J. Thiem in "Jahrbuch der Biotechnologie", Karl Hanser: München, 1990, vol. 3, 114-120; K. G. I. Nilsson in "Enzymes in Carbohydrate Synthesis", eds. M. D. Bednarski and E. S. Simon, ACS Symposium Ser. 1991, 466, pp. 51-62; P. Stangier and J. Thiem , ACS Symposium Ser. 1991, 466, pp. 63-68; C.-H-Wong, R. L. Halcomb, Y. Ichikawa and T. Kajimoto, Angew. Chem., 1995, 107, 581-582; R. L. Halcomb in "Enzyme Catalysis in Organic Synthesis", eds. K. Drauz and H. Waldmann, VCh: Weinheim-New York-Basel-Cambridge-Tokyo, 1995, Vol. 1, pp. 303-306.
41. For an overview on enzymatic transglycosylations see: K. G. I. Nilsson, Trends Biotechnol., 1988, 6, 256-264; R. Stiller and J. Thiem in "Jahrbuch der Biotechnologie", Karl Hanser: München, 1990, vol. 3, 114-120; K. G. I. Nilsson in "Enzymes in Carbohydrate Synthesis", eds. M. D. Bednarski and E. S. Simon, ACS Symposium Ser. 1991, 466, pp. 51-62; P. Stangier and J. Thiem , ACS Symposium Ser. 1991, 466, pp. 63-68; C.-H-Wong, R. L. Halcomb, Y. Ichikawa and T. Kajimoto, Angew. Chem., 1995, 107, 581-582; R. L. Halcomb in "Enzyme Catalysis in Organic Synthesis", eds. K. Drauz and H. Waldmann, VCh: Weinheim-New York-Basel-Cambridge-Tokyo, 1995, Vol. 1, pp. 303-306.
42. For an overview on enzymatic transglycosylations see: K. G. I. Nilsson, Trends Biotechnol., 1988, 6, 256-264; R. Stiller and J. Thiem in "Jahrbuch der Biotechnologie", Karl Hanser: München, 1990, vol. 3, 114-120; K. G. I. Nilsson in "Enzymes in Carbohydrate Synthesis", eds. M. D. Bednarski and E. S. Simon, ACS Symposium Ser. 1991, 466, pp. 51-62; P. Stangier and J. Thiem , ACS Symposium Ser. 1991, 466, pp. 63-68; C.-H-Wong, R. L. Halcomb, Y. Ichikawa and T. Kajimoto, Angew. Chem., 1995, 107, 581-582; R. L. Halcomb in "Enzyme Catalysis in Organic Synthesis", eds. K. Drauz and H. Waldmann, VCh: Weinheim-New York-Basel-Cambridge-Tokyo, 1995, Vol. 1, pp. 303-306.
43. For an overview on enzymatic transglycosylations see: K. G. I. Nilsson, Trends Biotechnol., 1988, 6, 256-264; R. Stiller and J. Thiem in "Jahrbuch der Biotechnologie", Karl Hanser: München, 1990, vol. 3, 114-120; K. G. I. Nilsson in "Enzymes in Carbohydrate Synthesis", eds. M. D. Bednarski and E. S. Simon, ACS Symposium Ser. 1991, 466, pp. 51-62; P. Stangier and J. Thiem , ACS Symposium Ser. 1991, 466, pp. 63-68; C.-H-Wong, R. L. Halcomb, Y. Ichikawa and T. Kajimoto, Angew. Chem., 1995, 107, 581-582; R. L. Halcomb in "Enzyme Catalysis in Organic Synthesis", eds. K. Drauz and H. Waldmann, VCh: Weinheim-New York-Basel-Cambridge-Tokyo, 1995, Vol. 1, pp. 303-306.
44. For an overview on enzymatic transglycosylations see: K. G. I. Nilsson, Trends Biotechnol., 1988, 6, 256-264; R. Stiller and J. Thiem in "Jahrbuch der Biotechnologie", Karl Hanser: München, 1990, vol. 3, 114-120; K. G. I. Nilsson in "Enzymes in Carbohydrate Synthesis", eds. M. D. Bednarski and E. S. Simon, ACS Symposium Ser. 1991, 466, pp. 51-62; P. Stangier and J. Thiem , ACS Symposium Ser. 1991, 466, pp. 63-68; C.-H-Wong, R. L. Halcomb, Y. Ichikawa and T. Kajimoto, Angew. Chem., 1995, 107, 581-582; R. L. Halcomb in "Enzyme Catalysis in Organic Synthesis", eds. K. Drauz and H. Waldmann, VCh: Weinheim-New York-Basel-Cambridge-Tokyo, 1995, Vol. 1, pp. 303-306.
45. O. Karthaus, S.-I. Shoda, H. Takano, K. Obata and S. Kobayashi, J. Chem. Soc. Perkin Trans. 1, 1994, 1851-1857; S.-I. Shoda, T. Kawasaki, K. Obata and S. Kobayashi, Carbohydr. Res., 1993, 249, 127-137 and references cited there.
46. O. Karthaus, S.-I. Shoda, H. Takano, K. Obata and S. Kobayashi, J. Chem. Soc. Perkin Trans. 1, 1994, 1851-1857; S.-I. Shoda, T. Kawasaki, K. Obata and S. Kobayashi, Carbohydr. Res., 1993, 249, 127-137 and references cited there.
47. M. Hrmova, G. B. Fincher, J.-L. Viladot, A. Planas and H. Driguez, J. Chem. Soc. Perkin Trans. 1, 1998, 3571-3576; J.-L. Viladot, V. Moreau, A. Planas and H. Driguez, J. Chem. Soc. Perkin Trans. 1, 1997, 2383-2387.
48. M. Hrmova, G. B. Fincher, J.-L. Viladot, A. Planas and H. Driguez, J. Chem. Soc. Perkin Trans. 1, 1998, 3571-3576; J.-L. Viladot, V. Moreau, A. Planas and H. Driguez, J. Chem. Soc. Perkin Trans. 1, 1997, 2383-2387.
49. S. Kobayashi, S.-I. Shoda, X. Wen, E. Okamoto and T. Kiyosada, J. Macromol. Sci., Pure Appl. Chem., 1997, A34, 2135-2142 [CA 127: 331639r]; S.-I. Shoda, Cellul. Commun., 1997, 4, 123-127 [CA 128: 36087j]; S. Kobayashi and S.-I. Shoda, New Macromol. Archit. Funct., Proc. OUMS'95, 1996, 171-180 [CA 127: 17863x]; S.-I. Shoda, E. Okamoto, M. Fujita, S. Osada, K. Ito, Z. Z. Abidin and S. Kobayashi, Korea Polym. J., 1996, 4, 112-116 [CA 126: 171797q].
50. S. Kobayashi, S.-I. Shoda, X. Wen, E. Okamoto and T. Kiyosada, J. Macromol. Sci., Pure Appl. Chem., 1997, A34, 2135-2142 [CA 127: 331639r]; S.-I. Shoda, Cellul. Commun., 1997, 4, 123-127 [CA 128: 36087j]; S. Kobayashi and S.-I. Shoda, New Macromol. Archit. Funct., Proc. OUMS'95, 1996, 171-180 [CA 127: 17863x]; S.-I. Shoda, E. Okamoto, M. Fujita, S. Osada, K. Ito, Z. Z. Abidin and S. Kobayashi, Korea Polym. J., 1996, 4, 112-116 [CA 126: 171797q].
51. S. Kobayashi, S.-I. Shoda, X. Wen, E. Okamoto and T. Kiyosada, J. Macromol. Sci., Pure Appl. Chem., 1997, A34, 2135-2142 [CA 127: 331639r]; S.-I. Shoda, Cellul. Commun., 1997, 4, 123-127 [CA 128: 36087j]; S. Kobayashi and S.-I. Shoda, New Macromol. Archit. Funct., Proc. OUMS'95, 1996, 171-180 [CA 127: 17863x]; S.-I. Shoda, E. Okamoto, M. Fujita, S. Osada, K. Ito, Z. Z. Abidin and S. Kobayashi, Korea Polym. J., 1996, 4, 112-116 [CA 126: 171797q].
52. S. Kobayashi, S.-I. Shoda, X. Wen, E. Okamoto and T. Kiyosada, J. Macromol. Sci., Pure Appl. Chem., 1997, A34, 2135-2142 [CA 127: 331639r]; S.-I. Shoda, Cellul. Commun., 1997, 4, 123-127 [CA 128: 36087j]; S. Kobayashi and S.-I. Shoda, New Macromol. Archit. Funct., Proc. OUMS'95, 1996, 171-180 [CA 127: 17863x]; S.-I. Shoda, E. Okamoto, M. Fujita, S. Osada, K. Ito, Z. Z. Abidin and S. Kobayashi, Korea Polym. J., 1996, 4, 112-116 [CA 126: 171797q].
53. rd ed., pp. 241-246.
54. J. E. G. Barnett, Biochem. J., 1967, 105, 669-672.
55. H. Matsui, Y. Tanaka, C. F. Brewer, J. S. Blanchard and E. J. Hehre, Carbohydr. Res., 1993, 250, 45-56; for other essential work of this group on the hydrolysis of glycosyl fluorides using enzymes see Y. Tanaka, W. Tao, J. S. Blanchard and E. J. Hehre, J. Biol. Chem., 1994, 269, 32306-32312 and references cited therein.
56. H. Matsui, Y. Tanaka, C. F. Brewer, J. S. Blanchard and E. J. Hehre, Carbohydr. Res., 1993, 250, 45-56; for other essential work of this group on the hydrolysis of glycosyl fluorides using enzymes see Y. Tanaka, W. Tao, J. S. Blanchard and E. J. Hehre, J. Biol. Chem., 1994, 269, 32306-32312 and references cited therein.
57. M. Albert, J. Ortner, B. J. Paul, W. Repetschnigg, W. Steiner, H. Weber and K. Dax, presented at the 19th International Carbohydrate Symposium, August 9-14, 1998, San Diego, USA [Abstract AP 090]; manuscript in preparation.
58. Unpublished results; compare: S.-I. Shoda, K. Obata, O. Karthaus and S. Kobayashi, J. Chem. Soc., Chem. Commun., 1993, 1402-1404.
59. From the anomeric mixture of per-O-acetylated mannosyl fluorides, obtained by reaction of 2,3,4,6-tetra-O-acetyl-D-mannopyranose with DAST, the β-anomer crystallised from ethanol; after deprotection, pure β-D-mannopyranosyl fluoride could be obtained for the first time.
60. C. Eis, M. Albert, K. Dax and B. Nidetzky, FEBS-Lett., 1998, 440, 440-443.
61. I. P. Street, C. R. Armstrong and S. G. Withers, Biochemistry, 1986, 25, 6021-6027.
62. S. G. Withers, K. Rupitz and I. P. Street, J. Biol. Chem., 1988, 263, 7929-7932; J. D. McCarter, M. J. Adam, N. G. Hartman and S. G. Withers, Biochem. J., 1994, 301, 343-348.
63. S. G. Withers, K. Rupitz and I. P. Street, J. Biol. Chem., 1988, 263, 7929-7932; J. D. McCarter, M. J. Adam, N. G. Hartman and S. G. Withers, Biochem. J., 1994, 301, 343-348.
64. T. K. Lindhorst, C. Braun and S. G. Withers, Carbohydr. Res., 1995, 268, 93-106; R. Mosi, S. He, J. Uitdehaag, B. W. Dijkstra and S. G. Withers, Biochemistry, 1997, 36, 9927-9934.
65. T. K. Lindhorst, C. Braun and S. G. Withers, Carbohydr. Res., 1995, 268, 93-106; R. Mosi, S. He, J. Uitdehaag, B. W. Dijkstra and S. G. Withers, Biochemistry, 1997, 36, 9927-9934.
66. J. D. McCarter and S. G. Withers, J. Am. Chem. Soc., 1996, 118, 241-242.
67. A. E. Stütz, Angew. Chem., 1996, 108, 2054-2056.
68. Q. Wang, R. W. Graham, D. Trimbur, R. A. J. Warren and S. Withers, J. Am. Chem. Soc., 1994, 116, 11594-11595; L. F. Mackenzie, Q. Wang, R. A. J. Warren and S. G. Withers, J. Am. Chem. Soc., 1998, 120, 5583-5584 and references cited therein; see also: S. G. Withers, L. Mackenzie and Q. Wang, PCT Int. Appl. WO 97 21,822 [CA 127: 132736v].
69. Q. Wang, R. W. Graham, D. Trimbur, R. A. J. Warren and S. Withers, J. Am. Chem. Soc., 1994, 116, 11594-11595; L. F. Mackenzie, Q. Wang, R. A. J. Warren and S. G. Withers, J. Am. Chem. Soc., 1998, 120, 5583-5584 and references cited therein; see also: S. G. Withers, L. Mackenzie and Q. Wang, PCT Int. Appl. WO 97 21,822 [CA 127: 132736v].
70. Q. Wang, R. W. Graham, D. Trimbur, R. A. J. Warren and S. Withers, J. Am. Chem. Soc., 1994, 116, 11594-11595; L. F. Mackenzie, Q. Wang, R. A. J. Warren and S. G. Withers, J. Am. Chem. Soc., 1998, 120, 5583-5584 and references cited therein; see also: S. G. Withers, L. Mackenzie and Q. Wang, PCT Int. Appl. WO 97 21,822 [CA 127: 132736v].
71. M. D. Burkart, Z. Zhang, S.-C. Hung and C.-H. Wong, J. Am. Chem. Soc., 1997, 119, 11743-11746.
72. The NMR-data given for benzoyl-protected 24 are those from the corresponding acetylated analog; the spectral data of 23 are reported to be consistant with those given in a reference, where (partial) data of D-mannofuranosyl fluorides can be found only.
73. Y. Takahashi, S. Tsuneda, T. Tsuchiya, Y. Koyama and S. Umezawa, Carbohydr. Res., 1992, 232, 89-105; Y. Kobayashi, T. Tsuchiya, T. Ohgi, N. Taneichi and Y. Koyama, Carbohydr. Res., 1992, 230, 89-105; E. Umemura, T. Tsuchiya, Y. Kobayashi and K. Tanaka, Carbohydr. Res., 1992, 224, 141-163; Y. Takahashi, T. Tsuchiya, S. Umezawa and H. Umezawa, Carbohydr. Res., 1991, 210, 221-232.
74. Y. Takahashi, S. Tsuneda, T. Tsuchiya, Y. Koyama and S. Umezawa, Carbohydr. Res., 1992, 232, 89-105; Y. Kobayashi, T. Tsuchiya, T. Ohgi, N. Taneichi and Y. Koyama, Carbohydr. Res., 1992, 230, 89-105; E. Umemura, T. Tsuchiya, Y. Kobayashi and K. Tanaka, Carbohydr. Res., 1992, 224, 141-163; Y. Takahashi, T. Tsuchiya, S. Umezawa and H. Umezawa, Carbohydr. Res., 1991, 210, 221-232.
75. Y. Takahashi, S. Tsuneda, T. Tsuchiya, Y. Koyama and S. Umezawa, Carbohydr. Res., 1992, 232, 89-105; Y. Kobayashi, T. Tsuchiya, T. Ohgi, N. Taneichi and Y. Koyama, Carbohydr. Res., 1992, 230, 89-105; E. Umemura, T. Tsuchiya, Y. Kobayashi and K. Tanaka, Carbohydr. Res., 1992, 224, 141-163; Y. Takahashi, T. Tsuchiya, S. Umezawa and H. Umezawa, Carbohydr. Res., 1991, 210, 221-232.
76. Y. Takahashi, S. Tsuneda, T. Tsuchiya, Y. Koyama and S. Umezawa, Carbohydr. Res., 1992, 232, 89-105; Y. Kobayashi, T. Tsuchiya, T. Ohgi, N. Taneichi and Y. Koyama, Carbohydr. Res., 1992, 230, 89-105; E. Umemura, T. Tsuchiya, Y. Kobayashi and K. Tanaka, Carbohydr. Res., 1992, 224, 141-163; Y. Takahashi, T. Tsuchiya, S. Umezawa and H. Umezawa, Carbohydr. Res., 1991, 210, 221-232.
77. H. Umezawa, Adv. Carbohydr. Chem. Biochem., 1974, 30, 183-225.
78. M. Sharma, R. J. Bernacki, M. J. Hillman and W. Korytnyk, Carbohydr. Res., 1993, 240, 85-93.
79. G. Saischek, F. Fuchs, K. Dax and G. Billiani, Eur. Pat. Appl. 91105231.4 (03. 04. 91) 0450585 A2 [CA 116:42980]; within the first step, use was made of a triflate-nitrite inversion reaction [R. Albert, K. Dax, R. W. Link and A. E. Stütz, Carbohydr. Res., 1983, 118, c5-c6].
80. G. Saischek, F. Fuchs, K. Dax and G. Billiani, Eur. Pat. Appl. 91105231.4 (03. 04. 91) 0450585 A2 [CA 116:42980]; within the first step, use was made of a triflate-nitrite inversion reaction [R. Albert, K. Dax, R. W. Link and A. E. Stütz, Carbohydr. Res., 1983, 118, c5-c6].
81. M. S. Motawia and E. B. Pedersen, Liebig's Ann. Chem., 1990, 1137-1139; the α-anomer - in contrast to the reported reaction -refuses inversion by these means.
82. R. Peinsipp, G. Koller and K. Dax, unpublished results.
83. H. H. Baer, F. Hernandez Mateo and L. Siemsen, Carbohydr. Res., 1989, 187, 67-92.
84. G. W. J. Fleet and L. C. Seymour, Tetrahedron Lett., 1987, 28, 3015-3018.
85. P. Borrachero-Moya, F. Cabrera-Escribano, M. Gomez-Guillen and F. Madrid-Diaz, Tetrahedron Lett., 1997, 38, 1231-1234.
86. K. C. Nicolaou, T. Ladduwahetty, J. L. Randall and A. Chucholowski, J. Am. Chem. Soc., 1986, 108, 2466-2467. In own experiments, 1,2-alkoxy group migrations reported herein to take place also when setting out from an L-arabinopyranoside derivative could not be reproduced, but led to ring-contracted products of type 43 exclusively.
87. I. P. Street and S. G. Withers, Can. J. Chem., 1986, 64, 1400-1403.
88. 1,2 is 5.9 Hz [R. Madsen and B. Fraser-Reid, J. Org. Chem., 1995, 60, 772-779].
89. T. J. Tewson, J. Org. Chem., 1983, 48, 3507-3510.
90. Only when applying high reaction temperature, α-anomers were - in a minor proportion - also subject to nucleophilic attack at C-2.
91. S. Schuppler, Thesis for Diploma, Technical University Graz, 1994.
92. Although from the kinetically controlled glycosidation an α:β-ratio of approximately 1:4 is obtained, the mixture can be quantitatively transformed into pure α-anomer by treatment with tert.-butyl magnesium chloride in ether [M. Kawana, H. Kuzuhara and S. Emoto, Bull. Chem. Soc. Jpn., 1981, 54, 1492-1504]. For safety reasons, the whole synthesis can be started from methyl α-D-ribofuranoside, which is easily accessible by the 1-O-alkylation approach [R. R. Schmidt, Angew. Chem., 1986, 98, 216-217] or a Koenigs-Knorr reaction [K. Bock and S. Refn, Acta Chem. Scand., 1988, B42, 324-327].
93. Although from the kinetically controlled glycosidation an α:β-ratio of approximately 1:4 is obtained, the mixture can be quantitatively transformed into pure α-anomer by treatment with tert.-butyl magnesium chloride in ether [M. Kawana, H. Kuzuhara and S. Emoto, Bull. Chem. Soc. Jpn., 1981, 54, 1492-1504]. For safety reasons, the whole synthesis can be started from methyl α-D-ribofuranoside, which is easily accessible by the 1-O-alkylation approach [R. R. Schmidt, Angew. Chem., 1986, 98, 216-217] or a Koenigs-Knorr reaction [K. Bock and S. Refn, Acta Chem. Scand., 1988, B42, 324-327].
94. Although from the kinetically controlled glycosidation an α:β-ratio of approximately 1:4 is obtained, the mixture can be quantitatively transformed into pure α-anomer by treatment with tert.-butyl magnesium chloride in ether [M. Kawana, H. Kuzuhara and S. Emoto, Bull. Chem. Soc. Jpn., 1981, 54, 1492-1504]. For safety reasons, the whole synthesis can be started from methyl α-D-ribofuranoside, which is easily accessible by the 1-O-alkylation approach [R. R. Schmidt, Angew. Chem., 1986, 98, 216-217] or a Koenigs-Knorr reaction [K. Bock and S. Refn, Acta Chem. Scand., 1988, B42, 324-327].
95. Reaction [48] of 3,4,6-tri-O-benzyl-D-mannopyranose had led to formation of the corresponding 2-deoxy-2-fluoro-β-D-glucopyranosyl fluoride (36%) together with α-D-mannopyranosyl fluoride (18%).
96. K. Shanmuganathan, T. Koudriakova, S. Nampalli, J. Du, J. M. Gallo, R. F. Shinazi and C. K. Chu, J. Med. Chem., 1994, 37, 821-827.
97. M. Bols and I. Lundt, Acta Chem. Scand., 1990, 44, 252-256; M. Bols, I. Lundt and E. R. Ottosen, Carbohydr. Res., 1991, 222, 141-149.
98. M. Bols and I. Lundt, Acta Chem. Scand., 1990, 44, 252-256; M. Bols, I. Lundt and E. R. Ottosen, Carbohydr. Res., 1991, 222, 141-149.
99. M. Bols and W. A. Szarek, J. Chem. Soc., Chem. Commun., 1992, 445-446.
100. A. Mikhailopulo, G. G. Sivets, N. E. Poopeiko and N. B. Khripach, Carbohydr. Res., 1995, 278, 71-89; A. Mikhailopulo, G. G. Sivets, N. E. Poopeiko and N. B. Khripach, Nucleos.-Nucleot., 1995, 14, 381-382; I. A. Mikhailopulo, N. E. Poopeiko, G. G. Sivets and N. B. Khripach, Nucleos.-Nucleot, 1995, 14, 383-384.
101. A. Mikhailopulo, G. G. Sivets, N. E. Poopeiko and N. B. Khripach, Carbohydr. Res., 1995, 278, 71-89; A. Mikhailopulo, G. G. Sivets, N. E. Poopeiko and N. B. Khripach, Nucleos.-Nucleot., 1995, 14, 381-382; I. A. Mikhailopulo, N. E. Poopeiko, G. G. Sivets and N. B. Khripach, Nucleos.-Nucleot, 1995, 14, 383-384.
102. A. Mikhailopulo, G. G. Sivets, N. E. Poopeiko and N. B. Khripach, Carbohydr. Res., 1995, 278, 71-89; A. Mikhailopulo, G. G. Sivets, N. E. Poopeiko and N. B. Khripach, Nucleos.-Nucleot., 1995, 14, 381-382; I. A. Mikhailopulo, N. E. Poopeiko, G. G. Sivets and N. B. Khripach, Nucleos.-Nucleot, 1995, 14, 383-384.
103. K. W. Pankiewicz and K. A. Watanabe, J. Fluorine Chem., 1993, 64, 15-36 and references cited therein.
104. M. W. Hager and D. C. Liotta, Tetrahedron Lett., 1992, 33, 7083-7086.
105. A. A. Nikitenko, B. M. Arshava, I. E. Mikerin, Y. E. Raifeld, V. J. Lee and S. A. Lang, Jr., Tetrahedron Lett., 1992, 33, 7087-7088.
106. F. A. Davis and H. Qi, Tetrahedron Lett., 1996, 37, 4345-4348.
107. M. A. Siddiqui, V. E. Marquez, J. S. Driscoll and J. J. Barchi, Jr., Tetrahedron Lett., 1994, 35, 3263-3266; see also: M. Okabe, R. C. Sun, G. B. Zenchoff, J. Org. Chem., 1991, 56, 4392-4397.
108. M. A. Siddiqui, V. E. Marquez, J. S. Driscoll and J. J. Barchi, Jr., Tetrahedron Lett., 1994, 35, 3263-3266; see also: M. Okabe, R. C. Sun, G. B. Zenchoff, J. Org. Chem., 1991, 56, 4392-4397.
109. Y. Choi, K. Lee, J. H. Hong, R. F. Schinazi and C. K. Chu, Tetrahedron Lett., 1998, 39, 4437-4440.
110. F. Yan, B. V. Nguyen, C. York and T. Hudlicky, Tetrahedron, 1997, 53, 11541-11548.
111. S. Rozen, Chem. Rev., 1996, 96, 1717-1736 and references cited therein.
112. G. S. Lal, G. P. Pez and R. G. Syvret, Chem. Rev., 1996, 96, 1737-1755 and references cited therein.
113. M. Albert, K. Dax and J. Ortner, Tetrahedron, 1998, 54, 4839-4848.
114. J. Ortner, M. Albert, H. Weber and K. Dax, J. Carbohydr. Chem., 1999, in press.
115. The major differences are: formation of stable N-glycosyl compounds; participation of solvents as well as fluoride anions; stereoselectivitity in the reaction of tri-O-acetyl-D-galactal; reported yields.
116. M. Albert, J. Ortner, B. J. Paul and K. Dax, unpublished results.
117. R. Peinsipp, Ph.D. Thesis, Technical University Graz, 1997; in part: J. Ortner, R. Peinsipp, M. Albert, and K. Dax, presented at the 19th International Carbohydrate Symposium, August 9-14, 1998, San Diego, USA [Abstract BP 169]; manuscript in preparation.
118. M. Albert, J. Ortner and K. Dax, presented at the 19th International Carbohydrate Symposium, August 9-14, 1998, San Diego, USA [Abstract BP 044]; manuscript in preparation.
119. H. Kodama, Y. Kajihara, T. Endo and H. Hashimoto, Tetrahedron Lett., 1993, 34, 6419-6422.
120. T. Hayashi, B. W. Murray, R. Wang and C.-H. Wong, Bioorg. & Med. Chem., 1997, 5, 497-500.
121. J. D. McCarter, W. Yeung, J. Chow, D. Dolphin and S. G. Withers, J. Am. Chem. Soc., 1997, 119, 5792-5797.
122. S. Cottaz, P. Rollin and H. Driguez, Carbohydr. Res., 1997, 298, 127-130.
123. J. D. McCarter, M. J. Adam and S. G. Withers, Carbohydr. Res., 1995, 266, 273-277.
124. J. A. L. M. van Dorst, A. F. Voskamp, J. P. Kamerling and J. F. G. Vliegenthart, Liebig's Ann./Recueil, 1997, 1227-1233 and previous papers cited therein.