1-O-vinyl glycosides via Tebbe olefination, their use as chiral auxiliaries and monomers

Journal of Organic Chemistry

Volumn 71, Issue 15, 2006, Pages 5457-5467

  Yuan, Jialong ^a   Lindner, Kristof ^a   Frauenrath, Holger ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

-O-VINYL GLYCOSIDES; ACETATE; ANOMERIC FORMATE GROUP; TEBBE OLEFINATION;

MATHEMATICAL MODELS; MONOMERS; OLEFINS; POLARIZATION; REACTION KINETICS; STEREOCHEMISTRY;

METABOLITES;

1 O VINYL GLYCOSIDE; ACETIC ACID; BENZOIC ACID; BIOMATERIAL; COPOLYMER; DICHLOROKETENE; FORMIC ACID; FUNCTIONAL GROUP; GLYCOSIDE; KETENE DERIVATIVE; MALEIC ANHYDRIDE; MONOMER; POLY(VINYL ALCOHOL MALEIC ANHYDRIDE); POLY(VINYL GLYCOSIDE); UNCLASSIFIED DRUG; VINYL 2,3,4,6 TETRA O BENZOYL ALPHA DEXTRO MANNOPYRANOSIDE; VINYL DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHIRALITY; CYCLOADDITION; GLYCOSYLATION; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; OLEFINATION; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS; TEBBE REACTION;

ALKENES; GLYCOSIDES; MANNOSIDES; MODELS, CHEMICAL; MOLECULAR STRUCTURE; POLYVINYL CHLORIDE; STEREOISOMERISM;

EID: 33746359994     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0600510     Document Type: Article

References (54)

1. (a) Ladmiral, V.; Melia, E.; Haddleton, D. M. Eur. Polym. J. 2004, 40, 431-449.
2. (b) Wulff, G.; Schmid, J.; Venhoff, T. Macromol. Chem. Phys. 1996, 197, 259-274.
3. (a) Leeuwenburgh, M. A.; van der Marel, G. A.; Overkleeft, H. S. Curr. Opin. Chem. Biol. 2003, 7, 757-765.
4. (b) Kodokawa, J.; Tagaya, H.; Chiba, K. Synlett 1999, 1845-1856.
5. (c) Roy, R. Curr. Opin. Struct. Biol. 1996, 6, 692-702.
6. Horejsi, V.; Smolek, P.; Kocourek, J. Biochim. Biophys. Acta 1978, 538, 293-298.
7. (a) Ambrosi, M.; Batsanov, A. S.; Cameron, N. R.; Davis, B. G.; Howard, J. A. K.; Hunter, R. J. Chem. Soc., Perkin Trans. 1 2002, 45-52.
8. (b) Loykulnant, S.; Yamashiro, M.; Hirao, A. Macromol. Chem. Phys. 2001, 202, 1791-1798.
9. (c) Wulff, G.; Zhu, L.; Schmidt, H. Macromolecules 1997, 30, 0, 4533-4539.
10. (a) Bernard, J.; Hao, X.; Davis, T. P.; Barner-Kowollik, C.; Stenzel, M. H. Biomacromolecules 2006, 7, 232-238.
11. (b) Albertin, L.; Stenzel, M. H.; Barner-Kowollik, C.; Foster, L. J. R.; Davis, T. P. Macromolecules 2005, 38, 9075-9084.
12. (c) Albertin, L.; Stenzel, M.; Barner-Kowollik, C.; Foster, L. J. R.; Davis, T. P. Macromolecules 2004, 37, 7530-7537.
13. (d) Muthukrishnan, S.; Jutz, G.; Andre, X.; Mori, H.; Müller, A. H. E. Macromolecules 2005, 38, 9-18.
14. (e) Muthukrishnan, S.; Mori, H.; Müller, A. H. E. Macromolecules 2005, 38, 3108-3119.
15. (f) Muthukrishnao, S.; Zhang, M.; Burkhardt, M.; Drechsler, M.; Mori, H.; Müller, A. H. E. Macromolecules 2005, 38, 7926-7934.
16. (a) Yamada, K.; Minoda, M.; Fukuda, T.; Miyamoto, T. J. Polym. Sci., Part A: Polym. Chem. 2001, 39, 459-467.
17. (b) Yamada, K.; Minoda, M.; Miyamoto, T. Macromolecules 1999, 32, 3553-3558.
18. (c) Yamada, K.; Yamaoka, K.; Minoda, M.; Miyamoto, T. J. Polym. Sci., Part A: Polym. Chem. 1997, 35, 255-261.
19. (d) Yamada, K.; Minoda, M.; Miyamoto, T. J. Polym. Sci., Part A: Polym. Chem. 1997, 35, 751-757.
20. Albertin, L.; Kohlert, C.; Stenzel, M.; Foster, L. J. R.; Davis, T. P. Biomacromolecules 2004, 5, 255-260.
21. Cao, S.; Roy, R. Tetrahedron Lett. 1996, 37, 3421-3424.
22. Roy, R.; Park, W. K. C.; Srivastava, O. P.; Foxall, C. Bioorg. Med. Chem. Lett. 1996, 6, 1399-1402.
23. Yoshida, T.; Akasaka, T.; Choi, Y.; Hattori, K.; Yu, B.; Mimura, T.; Kaneko, Y.; Nakashima, H.; Aragaki, E.; Premanathan, M.; Yamamoto, N.; Uryu, T. J. Polym. Sci., Part A: Polym. Chem. 1999, 37, 789-800.
24. (a) Dettinger, H. M.; Lehmann, J.; Wallenfels, K. Carbohydr. Res. 1980, 87, 63-70.
25. (b) De Raadt, A.; Ferner, R. J. Carbohydr. Res. 1991, 216, 93-107.
26. Handerson, S.; Schlaf, M. Org. Lett. 2002, 4, 407-409.
27. Perrine, T. D.; Glaudemans, C. P. J.; Ness, R. K.; Kyle, J.; Fletcher, H. G., Jr. J. Org. Chem. 1967, 32, 664-669.
28. Rollin, P.; Bencomo, V. V.; Sinay, P. Synthesis 1984, 134-135.
29. (a) Edathil, J.; Nguyen, J.; Hughes, K.; Boyko, W. J.; Giuliano, R. M. J. Carbohydr. Chem. 2001, 20, 81-85.
30. (b) Hughes, K. D.; Nguyen, T.-L. N.; Dyckman, D.; Dulay, D.; Boyko, W. J.; Giuliano, R. M. Tetrahedron: Asymmetry 2005, 16, 273-282.
31. Cottier, L.; Remy, G.; Descotes, G. Synthesis 1979, 711-712.
32. Marra, A.; Esnault, J.; Veyrieres, A.; Sinay, P. J. Am. Chem. Soc. 1992, 114, 6354-6360.
33. Chenault, H. K.; Castro, A.; Chafin, L. F.; Yang, J. J. Org. Chem. 1996, 61, 5024-5031.
34. Larsen, D. S.; Stoodley, R. J. J. Chem. Soc., Perkin Trans. 1 1989, 1841-1852.
35. Hartley, R. C.; McKiernan, G. J. J. Chem. Soc., Perkin Trans, 1 2002, 2763-2793.
36. (a) Brady, W. T.; Watts, R. D. J. Org. Chem. 1980, 45, 3525-3527.
37. (b) Brady, W. T. Tetrahedron 1981, 37, 2949-2966.
38. (a) Greene, A. E.; Charbonnier, F.; Luche, M. J.; Moyano, A. J. Am. Chem. Soc. 1987, 109, 4752-4753.
39. (b) De Azevedo, M. B. M.; Murta, M. M.; Greene, A. E. J. Org. Chem. 1992, 57, 4567-4569.
40. Ganz, I.; Kunz, H. Synthesis 1994, 1353-1358.
41. (a) James, V. J.; Stevens, J. D. Carbohydr. Res. 1972, 21, 334-335.
42. (b) Horton, D.; Durette, P. L. Carbohydr. Res. 1971, 18, 57-80.
43. The three-letter code refers to the orientation of the anomeric group (equatorial or axial) and the conformation (gauche or trans) of the anomeric group in relation to O-5 and C-2, respectively.
44. (a) Tvaroska, I.; Kozar, T. J. Am. Chem. Soc, 1980, 102, 6929-6936.
45. (b) Tvaroska, I.; Kozar, T. Carbohydr. Res, 1981, 90, 173-185.
46. Beyer, U.; Müller, F. H.; Ringsdorf, H. Makromol. Chem. 1967, 101, 74-90.
47. (a) Tsukino, M.; Kunitake, T. Polym. J. 1979, 11, 437-447.
48. (b) Tsukino, M.; Kunitake, T. Polym. J. 1985, 17, 943-951.
49. (a) Schlüter, A. D.; Rabe, J. P. Angew. Chem., Int. Ed. 2000, 39, 864-883.
50. (b) Frauenrath, H. Prog. Polym. Sci. 2005, 30, 325-384.
51. (a) Baldwin, M. G. J. Polym. Sci. 1965, 3, 703-710.
52. (b) Hallensleben, M. L. Makromol. Chem. 1971, 144, 267-281.
53. (c) Hao, X.-J.; Fujimori, K.; Henry, P. C. Macromol. Rapid Commun. 2001, 22, 111-113.
54. Tebbe, F. N.; Parshall, G. W.; Reddy, G. S. J. Am. Chem. Soc. 1978, 100, 3611-3613.