Synthesis of Anomeric Sulfur Analogues of CMP-Neu5Ac Containing Tethered Alkane or Arene

Synlett

Volumn , Issue 1, 2004, Pages 37-40

  Chang, Kai Hsuan ^a   Tao, Ying Shin ^a   Li, Wen Shan ^a  

^a INSTITUTE OF CHEMISTRY   (Taiwan)

Author keywords

Hydroxyalkyl (aryl) thioglycosides; Selective deprotection; Sialylation; Sialyltransferase

Indexed keywords

ALKANE DERIVATIVE; CYTIDINE PHOSPHATE; ESTER DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; SIALIC ACID DERIVATIVE; SULFUR DERIVATIVE; THIOGLYCOSIDE; TRICHLOROACETIC ACID;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; OXIDATION; SIALYLATION; STEREOCHEMISTRY; TECHNIQUE;

EID: 0347595309     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-43349     Document Type: Article

References (36)

1. (a) Philips, M.; Nudelman, E.; Gaeta, F. C. A.; Perez, M.; Singhal, A. K.; Hakomori, S.; Paulson, J. C. Science 1990, 250, 1130.
2. (b) Walz, G.; Aruffo, A.; Kolanus, W.; Bevilacqua, M.; Seed, B. Science 1990, 250, 1132.
3. (c) Varki, A. Glycobiology 1993, 3, 97.
4. (d) Rosenberg, A. In Biological of Sialic Acids; Plenum Press: New York, 1995.
5. (e) Schauer, R.; Kamerling, J. P. In Glycoproteins II; Montreuil, J.; Vliegenthart, J. F. G.; Schachter, H., Eds.; Elsevier: Amsterdam, 1997, 243-402.
6. (f) Dennis, J. W.; Granovsky, M.; Warren, C. E. BioEssays 1999, 21, 412.
7. (g) Bertozzi, C. R.; Kiessling, L. L. Science 2001, 291, 2357.
8. Hildebrandt, H.; Becker, C.; Gluer, S.; Rosner, H.; GerardySchahn, R.; Rahmann, H. Cancer Res. 1998, 58, 779.
9. Gessner, P.; Riedl, S.; Quentmaier, A.; Kemmer, W. Cancer Lett. 1993, 75, 143.
10. (a) Whalen, L. J.; McEvoy, K. A.; Halcomb, R. L. Bioorg. Med. Chem. Lett. 2003, 13, 301.
11. (b) Hinou, H.; Sun, X.-L.; Ito, Y. Tetrahedron Lett. 2002, 43, 9147.
12. (c) Tanaka, T.; Ozawa, M.; Miura, T.; Inazu, T.; Tsuji, S.; Kajimoto, T. Synlett 2002, 9, 1487.
13. (d) Schworer, R.; Schmidt, R. R. J. Am. Chem. Soc. 2002, 124, 1632.
14. (e) Wu, C.-Y.; Hsu, C.-C.; Chen, S.-T.; Tsai, Y.-C. Biochem. Biophys. Res. Commun. 2001, 284, 466.
15. (f) Sun, H.; Yang, J.; Amaral, K. E.; Horenstein, B. A. Tetrahedron Lett. 2001, 42, 2451.
16. (g) Schaub, C.; Muller, B.; Schmidt, R. R. Eur. J. Org. Chem. 2000, 9, 1745.
17. (h) Schröder, P. N.; Giannis, A. Angew. Chem. Int. Ed. 1999, 38, 1379.
18. (i) Muller, B.; Schaub, C.; Schmidt, R. R. Angew. Chem. Int. Ed. 1998, 37, 2893.
19. (j) Amann, F.; Schaub, C.; Muller, B.; Schmidt, R. R. Chem.-Eur. J. 1998, 4, 1106.
20. (k) Schaub, C.; Muller, B.; Schmidt, R. R. Glycoconjugate J. 1998, 15, 345.
21. (l) Kleineidam, R. G.; Schmelter, T.; Schwarz, R. T.; Schauer, R. Glycoconjugate J. 1997, 14, 57.
22. (m) Hinou, H.; Sun, X.-L.; Ito, Y. J. Org. Chem. 2003, 68, 5602.
23. (a) Barone, A. D.; Tang, J. Y.; Caruthers, M. H. Nuclei Acids Res. 1984, 12, 4051.
24. (b) Kajihara, Y.; Ebata, T.; Koseki, K.; Kodama, H.; Matsushita, H.; Hashimoto, H. J. Org. Chem. 1995, 60, 5732.
25. (a) Eisele, T.; Toepfer, A.; Kretzschmar, G.; Schmidt, R. R. Tetrahedron Lett. 1996, 37, 1389.
26. (b) Kanie, O.; Nakamura, J.; Itoh, Y.; Kiso, M.; Hasegawa, A. J. Carbohydr. Chem. 1987, 6, 117.
27. (c) Turnbull, W. B.; Field, R. A. J. Chem. Soc., Perkin Trans. 1 2000, 1859.
28. For example, treatment of 4 and 2-mercaptoethyl trimethylsilyl ether (or 2-mercaptoethyl tertbutyldiphenylsilyl ether) with boron trifluoride in dichloromethane gave the desired thioglycoside in low yield, along with the formation of large amounts of bis-(2-trimethylsilyloxyethyl) disulfide or bis-(2-tertbutyldiphenylsilyloxyethyl) disulfide. Condensation of the 2-chlorosialic acid with the 2-mercaptoethyl benzoate gave the thioglycoside in low yield. The products were contaminated with the sialic acid 2,3-elimination product, see: (a) Moreau, V.; Norrild, J. C.; Driguez, H. Carbohydr. Res. 1997, 300, 271. (b) Sabesan, S.; Neira, S.; Davidson, F.; Duus, J.; Bock, K. J. Am. Chem. Soc. 1994, 116, 1616.
29. For example, treatment of 4 and 2-mercaptoethyl trimethylsilyl ether (or 2-mercaptoethyl tertbutyldiphenylsilyl ether) with boron trifluoride in dichloromethane gave the desired thioglycoside in low yield, along with the formation of large amounts of bis-(2-trimethylsilyloxyethyl) disulfide or bis-(2-tertbutyldiphenylsilyloxyethyl) disulfide. Condensation of the 2-chlorosialic acid with the 2-mercaptoethyl benzoate gave the thioglycoside in low yield. The products were contaminated with the sialic acid 2,3-elimination product, see: (a) Moreau, V.; Norrild, J. C.; Driguez, H. Carbohydr. Res. 1997, 300, 271. (b) Sabesan, S.; Neira, S.; Davidson, F.; Duus, J.; Bock, K. J. Am. Chem. Soc. 1994, 116, 1616.
30. Cohen, S. B.; Halcomb, R. L. J. Org. Chem. 2000, 65, 6145.
31. The required compounds 5a-d were prepared from corresponding mercaptoalkyl(aryl) alcohols, respectively, by treating them with trichloroacetyl chloride in dichloromethane at 0°C for 4 h.
32. 3eq of a β-linked alkyl thioglycoside of sialic acid diplayed a signal upfield relative to that of the corresponding α-anomer, see: (a) Ponpipom, M. M.; Bugianesi, R. L.; Shen, T. Y. Can. J. Chem. 1980, 58, 214. (b) Warner, T. G.; Lee, L. A. Carbohydr. Res. 1988, 176, 211.
33. 3eq of a β-linked alkyl thioglycoside of sialic acid diplayed a signal upfield relative to that of the corresponding α-anomer, see: (a) Ponpipom, M. M.; Bugianesi, R. L.; Shen, T. Y. Can. J. Chem. 1980, 58, 214. (b) Warner, T. G.; Lee, L. A. Carbohydr. Res. 1988, 176, 211.
34. Miyazaki, T.; Sato, H.; Sakakibara, T.; Kajihara, Y. J. Am. Chem. Soc. 2000, 122, 5678.
35. CMP-Neu5Ac mimetics that contain a spiro-ring.
36. 3): δ = 5. 89 (d, J = 9.3 Hz, 1 H), 5.44 (s, 1 H), 5.26 (td, J = 4.5, 11.0 Hz, 1 H), 5.21 (m, 1 H), 4.96 (dd, J = 2.1, 12.2 Hz, 1 H), 4.42 (d, J = 10.4 Hz, 1 H), 4.05 (m, 2 H), 3.77 (s, 3 H), 3.75 (m, 1 H), 3.62 (m, 1 H), 2.84 (m, 1 H), 2.76 (m, 1 H), 2.58 (br s, 1 H), 2.50 (dd, J = 4.7, 13.8 Hz, 1 H), 2.12 (m, 1 H), 2.10 (s, 3 H), 2.05 (s, 3 H), 2.00 (s, 3 H), 1.98 (s, 3 H), 1.84 (s, 3 H).