Synthesis of 3-deoxy-D-manno-2-octulosonic acid (Kdo) and D-glycero-D-talo-2-octulosonic acid (Ko) and their α-glycosides

Tetrahedron Asymmetry

Volumn 11, Issue 1, 2000, Pages 319-335

  Reiner, Martin ^a   Schmidt, Richard R ^a  

^a UNIVERSITY OF KONSTANZ   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

3 DEOXY MANNO OCTULOSONIC ACID; DISACCHARIDE; THIOGLYCOSIDE;

ARTICLE; CARBOHYDRATE ANALYSIS; CARBOHYDRATE SYNTHESIS; CHEMICAL MODIFICATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; PROTON TRANSPORT; REACTION ANALYSIS;

EID: 0034000120     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00557-1     Document Type: Article

References (35)

1. (a) Unger, F. M. Adv. Carbohydr. Chem. Biochem. 1981, 38, 323-388;
2. (b) Alexander, C.; Rietschel, E. T. Biospektrum 1999, 4, 275-282.
3. For syntheses of Kdo, see: (a) Frick, W.; Krülle, T.; Schmidt, R. R. Liebigs Ann. Chem. 1991, 435-438; (b) Burke, S. D.; Sametz, G. M. Org. Lett. 1999, 1, 71-74; and references cited therein.
4. For syntheses of Kdo, see: (a) Frick, W.; Krülle, T.; Schmidt, R. R. Liebigs Ann. Chem. 1991, 435-438; (b) Burke, S. D.; Sametz, G. M. Org. Lett. 1999, 1, 71-74; and references cited therein.
5. Recent Kdo syntheses not yet mentioned in Ref. 2: (a) Mikshiev, Y. M.; Paidak, B. B.; Kornilev, V. I.; Zhdanov, Y. A. Russ. J. Gen. Chem. 1998, 68, 1168-1169; (b) Bräuer, N.; Kirschning, A.; Schaumann, E. Eur. J. Org. Chem. 1998, 2729-2732.
6. Recent Kdo syntheses not yet mentioned in Ref. 2: (a) Mikshiev, Y. M.; Paidak, B. B.; Kornilev, V. I.; Zhdanov, Y. A. Russ. J. Gen. Chem. 1998, 68, 1168-1169; (b) Bräuer, N.; Kirschning, A.; Schaumann, E. Eur. J. Org. Chem. 1998, 2729-2732.
7. For Kdo glycoside syntheses, see: (a) Paulsen, H.; Brenken, M. Liebigs Ann. Chem. 1991, 1113-1116; (b) Rembold, H.; Schmidt, R. R. Carbohydr. Res. 1993, 246, 137-159; (c) D'Souza, F. W.; Kosma, P.; Brade, H. Carbohydr. Res. 1994, 262, 223-244; (d) Lay, L.; Nicotra, F.; Panza, L.; Russo, G.; Sello, G. J. Carbohydr. Chem. 1998, 17, 1269-1281; and references cited therein.
8. For Kdo glycoside syntheses, see: (a) Paulsen, H.; Brenken, M. Liebigs Ann. Chem. 1991, 1113-1116; (b) Rembold, H.; Schmidt, R. R. Carbohydr. Res. 1993, 246, 137-159; (c) D'Souza, F. W.; Kosma, P.; Brade, H. Carbohydr. Res. 1994, 262, 223-244; (d) Lay, L.; Nicotra, F.; Panza, L.; Russo, G.; Sello, G. J. Carbohydr. Chem. 1998, 17, 1269-1281; and references cited therein.
9. For Kdo glycoside syntheses, see: (a) Paulsen, H.; Brenken, M. Liebigs Ann. Chem. 1991, 1113-1116; (b) Rembold, H.; Schmidt, R. R. Carbohydr. Res. 1993, 246, 137-159; (c) D'Souza, F. W.; Kosma, P.; Brade, H. Carbohydr. Res. 1994, 262, 223-244; (d) Lay, L.; Nicotra, F.; Panza, L.; Russo, G.; Sello, G. J. Carbohydr. Chem. 1998, 17, 1269-1281; and references cited therein.
10. For Kdo glycoside syntheses, see: (a) Paulsen, H.; Brenken, M. Liebigs Ann. Chem. 1991, 1113-1116; (b) Rembold, H.; Schmidt, R. R. Carbohydr. Res. 1993, 246, 137-159; (c) D'Souza, F. W.; Kosma, P.; Brade, H. Carbohydr. Res. 1994, 262, 223-244; (d) Lay, L.; Nicotra, F.; Panza, L.; Russo, G.; Sello, G. J. Carbohydr. Chem. 1998, 17, 1269-1281; and references cited therein.
11. Kawahara, K.; Brade, H.; Rietschel, E. T.; Zähringer, U. Eur. J. Biochem. 1987, 163, 489-495.
12. Isshiki, Y.; Kawahara, K.; Zähringer, U. Carbohydr. Res. 1998, 313, 21-27; and references cited therein.
13. (a) Paulsen, H.; Krogmann, C.; v. Deesen, U. Liebigs Ann. Chem. 1988, 277-279;
14. (b) Gass, J.; Strobl, M.; Loibner, A.; Kosma, P.; Zähringer, U. Carbohydr. Res. 1993, 244, 69-84;
15. (c) Kosma, P.; Sebljic, H.; Balint, G. J. Carbohydr. Chem. 1996, 15, 701-714.
16. Schmidt, O. T. Methods Carbohydr. Chem. 1963, 2, 318.
17. Lerner, L. M. J. Org. Chem. 1976, 41, 2228-2229.
18. (a) Imoto, M.; Kusumoto, S.; Shiba, T. Tetrahedron Lett. 1987, 28, 6235-6238;
19. (b) van der Klein, P. A. M.; Boons, G. J. P. H.; Veeneman, G. N.; van der Marel, G.A.; van Boom, J. H. Tetrahedron Lett. 1989, 30, 5477-5480;
20. (c) van der Klein, P. A. M.; Filemon, W.; Boons, G. J. P. H.; Veeneman, G. H.; van der Marel, G. A.; van Boom, J. H. Tetrahedron 1992, 48, 4649-4658.
21. This compound is commercially available.
22. Braun, M.; Esdar, M. Chem. Ber. 1981, 114, 2924-2928; and references therein.
23. Reiner, M.; investigations for the Dissertation.
24. Barton, H. R. D., McCombie, W. S. J. Chem. Soc., Perkin Trans. 1 1995, 1574-1585.
25. For anomeric O-alkylation, see: (a) Schmidt, R. R.; Eßwein, A. Angew. Chem. 1988, 100, 1234-1236; (b) Angew. Chem. Int. Ed. 1988, 27, 1178-1180; and references cited therein.
26. For anomeric O-alkylation, see: (a) Schmidt, R. R.; Eßwein, A. Angew. Chem. 1988, 100, 1234-1236; (b) Angew. Chem. Int. Ed. 1988, 27, 1178-1180; and references cited therein.
27. Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277-7287.
28. Yin, H.; Franck, R. W.; Chen, S. L.; Quigley, G. J.; Todaro, L. J. J. Org. Chem. 1992, 57, 644-651.
29. Similar results were previously observed; see Ref. 10b, c.
30. (a) Kovác, P.; Alfödi, J.; Kosik, M. Chem. Zvesti. 1974, 28, 820;
31. (b) Chem. Abstr. 1975, 82, 112214x.
32. Handrecky, A.; Sinay, P. J. Org. Chem. 1992, 57, 4142-4151.
33. Eßwein, A.; Rembold, H.; Schmidt, R. R. Carbohydr. Res. 1990, 200, 287-305.
34. Eisele, T.; Ishida, H.; Hummel, G.; Schmidt, R. R. Liebigs Ann. Chem. 1995, 2113-2122.
35. Jiang, L.; Chan, T.-H. Tetrahedron Lett. 1998, 39, 355-358.