n-Pentenyl glycosyl orthoesters as versatile intermediates in oligosaccharide synthesis. The proteoglycan linkage region

Journal of the American Chemical Society

Volumn 121, Issue 2, 1999, Pages 468-469

  Allen, John G ^a   Fraser Reid, Bert ^b  

^a DUKE UNIVERSITY   (United States)

^b Nat Prod Glycotechnology Res I   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ESTER DERIVATIVE; N PENTENYLGLYCOSYL ORTHOESTER; OLIGOSACCHARIDE; PROTEOGLYCAN; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CYSTIC FIBROSIS; DECOMPOSITION; ESTERIFICATION; ISOMERISM; PROTEOGLYCAN SYNTHESIS; REACTION ANALYSIS; RHEUMATOID ARTHRITIS; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS;

EID: 0033585540     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9832358     Document Type: Article

References (55)

1. Functions of the Proteoglycans; Everd, D., Whelan, J., Eds.; Wiley: New York, 1986. Proteoglycans; Jollés, P., Ed.; Birkhäuser Verlag: Basel, Switzerland, 1994.
2. Functions of the Proteoglycans; Everd, D., Whelan, J., Eds.; Wiley: New York, 1986. Proteoglycans; Jollés, P., Ed.; Birkhäuser Verlag: Basel, Switzerland, 1994.
3. Hukins, D. W. L. Tissue components. In Connective Tissue Matrix; Hukins, D. W. L., Ed.; Verlag: Basel, Switzerland, 1984; p 1.
4. Burton, A. F. Amino Sugars. Quest for Health Series; 1990.
5. (a) Hirsh, J.; Levine, M. N. Blood 1992, 79, 1-17.
6. (b) Sie, P.; Dupouy, D.; Caranobe, C.; Petitou, M.; Boneu, B. Blood 1993, 81, 1771-1777.
7. Rodén, L. In The Biochemistry of Glycoproteins and Proteoglycans; Lannarz, W. J., Ed.; Plenum: New York, 1980; p 267.
8. Di Sant'Agnese, P. A.; Davis, P. B. New Engl. J. Med. 1976, 295, 597.
9. (a) Prehm, P. Biochem. J. 1983, 211, 181.
10. (b) Hascall, V. C. Introduction. In Functions of the proteoglycans; Evered, D., Whelan, J., Eds.; Wiley: New York, 1986; p 1.
11. Fedarko, N. S. Isolation and purification of proteoglycans. In Proteoglycans; Jollés, P., Ed.; Birkhäuser Verlag: Basel, Switzerland, 1994; p 9.
12. (a) Zhang, L.; Esko, J. D. J. Biol. Chem. 1994, 269, 19295.
13. (b) Zhang, L.; David, G.; Esko, J. D. J. Biol. Chem. 1995, 270, 27127.
14. (c) Lidholt, K.; Weinke, J. L.; Kiser, C. S.; Lugemwa, F. M.; Bame, K. J.; Cheifetz, K. J.; Massagué, J.; Lindahl, U.; Esko, J. D. Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 2267.
15. (a) Segarini, P. R., Seyedi, S. M. J. Biol. Chem. 1988, 263, 8366.
16. (b) Cheifetz, S.; Massagué, J. J. Biol. Chem. 1989, 264, 12025.
17. (c) Andres, J. L.; Ronnstrand, L.; Cheifetz, S.; Massagué, J. J. Biol. Chem. 1991, 266, 23282.
18. For some examples, see: (a) Goto, F.; Ogawa, T. Tetrahedron Lett. 1992, 33, 5099.
19. (b) Rio, S.; Beau, J.-M.; Jacquinet, J.-C. Carbohydr. Res. 1993, 244, 295.
20. (c) Rio, S.; Beau, J.-M.; Jacquinet, J.-C. Carbohydr. Res. 1991, 219, 71.
21. (d) Garegg, P. J.; Lindberg, B.; Norberg, T. Acta Chem. Scand. B 1979, 33, 449.
22. (e) Ekborg, G.; Curenton, T.; Krishna, N. R.; Rodén, L. J. Carbohydr. Chem. 1990, 9, 15.
23. (f) Nilsson, M.; Westman, J.; Svahn, C.-M. J. Carbohydr Res. 1993, 12, 23.
24. Fraser-Reid, B.; Udodong, U. E.; Wu, Z.; Ottosson, H.; Merritt, J. R.; Rao, C. S.; Roberts, C.; Madsen R. Synlett 1992, 927.
25. Roberts, C.; Madsen, R.; Fraser-Reid, B. J. Am. Chem. Soc. 1995, 117, 1546.
26. (a) Ramu, K.; Baker, J. K. J. Med. Chem. 1995, 38, 1911.
27. (b) Kanaoka, M.; Kato, H.; Yano, S. Chem. Pharm. Bull. 1990, 38, 221.
28. (c) Mattox, B. R.; Goodrich, J. E.; Nelson, A. N. Steroids 1982, 40, 23.
29. (d) Marra, A.; Bond, X.; Fetitou, M.; Sinay, P. Carbohydr. Res. 1989, 195, 39.
30. (e) Hashimoto, S.; Sano, A.; Umeo, K.; Nakajima, M.; Ikegani, S. Chem. Pharm. Bull. 1995, 43, 2267.
31. (f) van Boeckel, C. A. A.; Delbressine, L. P. C.; Kaspersen, F. M. Recl. Trav. Chim. Pays-Bas 1985, 104, 259.
32. This compound previously prepared: Udodong, U. E.; Rao, C. S.; Fraser-Reid, B. Tetrahedron 1992, 48, 4713.
33. (a) Vlahov, J.; Snatzke, G. Liebigs Ann. Chem. 1983, 570.
34. (b) Garegg, P. J.; Olsson, L.; Oscarson, S. J. Org. Chem. 1995, 60, 2200.
35. (a) Arsequell, G.; Sanies, N.; Valencia, G. Tetrahedron Lett. 1995, 36, 7323.
36. (b) Tabeur, C.; Machetto, F.; Mallet, J.-M.; Duchaussoy, P.; Petitou, M.; Sinay, P. Carbohydr. Res. 1996, 281, 253.
37. (c) Garegg., P. J.; Olsson, L.; Oscarson, S. Bioorg. Med. Chem. 1996, 4, 1867.
38. (d) Isogai, Y.; Kawase, T.; Ishida, H.; Kiso, M.; Hasegawa, A. J. Carbohydr. Chem. 1996, 15, 1001.
39. This transformation is usually achieved in two steps: (a) Ratcliffe, A. J.; Konradsson, P.; Fraser-Reid, B. Carbohydr. Res. 1991, 216, 323.
40. (b) Ratcliffe, A. J.; Konradsson, P.; Fraser-Reid, B. J. Am. Chem. Soc. 1990, 112, 5665.
41. (c) Ziegler, T.; Sutoris, H.; Glaudemans, P. J. Carbohydr. Res. 1992, 229, 271.
42. (d) Hashimoto, S.; Sakamoto, H.; Honda, T.; Ikegami, S. Tetrahedron Lett. 1997, 38, 5181.
43. (e) Moradei, O.; du Mortier, C.; Cirelli, A. F.; Thiem, J. J. Carbohydr. Chem. 1995, 14, 525.
44. Or in two steps without purification: (f) Nashed, E. M.; Glaudemans, C. P. J. J. Org. Chem. 1987, 52, 5255.
45. (g) Ziegler, T.; Pavliak, V.; Lin, T.-H.; Kovac, P.; Glaudemans, C. P. J. Carbohydr. Res. 1990, 204, 167. Please see Supporting Information for two more examples of this useful reaction performed in one pot.
46. Please see Supporting Information for unpublished work.
47. The disappointing yield of 56% was due to substantial transfer of chloroacetyl from 19 to the C4-OH of 11c. the resulting xylosyl 4-chloroacetate (11c, H = ClAc) being produced in 21% yield.
48. van Boeckel, C. A. A.; Beetz, T. Tetrahedron Lett. 1983, 24, 3775.
49. Merritt, J. R.; Debenham, J. S.; Fraser-Reid, B. J. Carbohydr. Chem. 1996, 15, 65.
50. 1H NMR spectrum and complete absence of the dibromide in MALDI-TOF and FAB mass spectra.
51. (a) Jansson, A. M.; Meldal, M.; Bock, K. Tetrahdron Lett. 1990, 48, 6991.
52. (b) Meldal, M.; Jensen, K. J. J. Chem. Soc. Chem. Commun. 1990, 483.
53. (c) Jansson, A. M.; Meldal, M.; Bock, K. Perkin Trans. 1 1992, 1699.
54. (a) Kisfaludy, L.; Schön, I. Synthesis 1983, 325.
55. (b) Schön, I.; Kisfaludy, L. Synthesis 1986, 303.