A new facile synthesis of C-4 nitrogen-containing derivatives of KDN2en and KDO2en

Synthesis

Volumn , Issue 7, 1997, Pages 769-772

  Kok, Gaik B ^a   Von Itzstein, Mark ^a  

^a MONASH UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

AZIDE; CARBOHYDRATE DERIVATIVE; SILANE DERIVATIVE; ULOSONIC ACID; UNCLASSIFIED DRUG;

CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL STRUCTURE; ENZYME ACTIVITY; ORGANIC CHEMISTRY; PROTON NUCLEAR MAGNETIC RESONANCE; REVIEW; SYNTHESIS;

EID: 0030873024     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-4471     Document Type: Review

References (24)

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9. Uchida, Y.; Tsukada, Y.; Sugimori, T. J. Biochem. 1984, 96, 507. Augé, C.; David, S.; Gautheron, C. Tetrahedron Lett. 1984, 25, 4663. Augé, C.; Gautheron, C. J. Chem. Soc., Chem. Commun. 1987, 859. Kim, M.-J.; Hennen, W. J.; Sweers, M.; Wong, C.-H. J. Am. Chem. Soc. 1988, 110, 6481. Augé, C.; David, S.; Malleron, A. Carbohydr. Res. 1989, 188, 201. Augé, C.; Gautheron, C.; David, S.; Malleron, A.; Cavayé, B.; Bouxon, B. Tetrahedron 1990, 46, 201. David, S.; Augé, C.; Gautheron, C. Adv. Carbohydr. Chem. and Biochem. 1991, 49, 175. Sparks, M. A.; Williams, K. W.; Lukacs, C.; Schnell, A.; Priebe, G.; Spaltenstein, A.; Whitesides, G. M. Tetrahedron 1993, 49, 1. Kragl, U.; Gödde, A.; Wandrey, C.; Kinzy, W.; Cappon, J. J.; Lugtenburg, J. Tetrahedron: Asymmetry 1993, 4, 1193. Kong, D. C. M.; von Itzstein, M. Tetrahedron Lett. 1995, 36, 957.
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11. Uchida, Y.; Tsukada, Y.; Sugimori, T. J. Biochem. 1984, 96, 507. Augé, C.; David, S.; Gautheron, C. Tetrahedron Lett. 1984, 25, 4663. Augé, C.; Gautheron, C. J. Chem. Soc., Chem. Commun. 1987, 859. Kim, M.-J.; Hennen, W. J.; Sweers, M.; Wong, C.-H. J. Am. Chem. Soc. 1988, 110, 6481. Augé, C.; David, S.; Malleron, A. Carbohydr. Res. 1989, 188, 201. Augé, C.; Gautheron, C.; David, S.; Malleron, A.; Cavayé, B.; Bouxon, B. Tetrahedron 1990, 46, 201. David, S.; Augé, C.; Gautheron, C. Adv. Carbohydr. Chem. and Biochem. 1991, 49, 175. Sparks, M. A.; Williams, K. W.; Lukacs, C.; Schnell, A.; Priebe, G.; Spaltenstein, A.; Whitesides, G. M. Tetrahedron 1993, 49, 1. Kragl, U.; Gödde, A.; Wandrey, C.; Kinzy, W.; Cappon, J. J.; Lugtenburg, J. Tetrahedron: Asymmetry 1993, 4, 1193. Kong, D. C. M.; von Itzstein, M. Tetrahedron Lett. 1995, 36, 957.
12. Uchida, Y.; Tsukada, Y.; Sugimori, T. J. Biochem. 1984, 96, 507. Augé, C.; David, S.; Gautheron, C. Tetrahedron Lett. 1984, 25, 4663. Augé, C.; Gautheron, C. J. Chem. Soc., Chem. Commun. 1987, 859. Kim, M.-J.; Hennen, W. J.; Sweers, M.; Wong, C.-H. J. Am. Chem. Soc. 1988, 110, 6481. Augé, C.; David, S.; Malleron, A. Carbohydr. Res. 1989, 188, 201. Augé, C.; Gautheron, C.; David, S.; Malleron, A.; Cavayé, B.; Bouxon, B. Tetrahedron 1990, 46, 201. David, S.; Augé, C.; Gautheron, C. Adv. Carbohydr. Chem. and Biochem. 1991, 49, 175. Sparks, M. A.; Williams, K. W.; Lukacs, C.; Schnell, A.; Priebe, G.; Spaltenstein, A.; Whitesides, G. M. Tetrahedron 1993, 49, 1. Kragl, U.; Gödde, A.; Wandrey, C.; Kinzy, W.; Cappon, J. J.; Lugtenburg, J. Tetrahedron: Asymmetry 1993, 4, 1193. Kong, D. C. M.; von Itzstein, M. Tetrahedron Lett. 1995, 36, 957.
13. Uchida, Y.; Tsukada, Y.; Sugimori, T. J. Biochem. 1984, 96, 507. Augé, C.; David, S.; Gautheron, C. Tetrahedron Lett. 1984, 25, 4663. Augé, C.; Gautheron, C. J. Chem. Soc., Chem. Commun. 1987, 859. Kim, M.-J.; Hennen, W. J.; Sweers, M.; Wong, C.-H. J. Am. Chem. Soc. 1988, 110, 6481. Augé, C.; David, S.; Malleron, A. Carbohydr. Res. 1989, 188, 201. Augé, C.; Gautheron, C.; David, S.; Malleron, A.; Cavayé, B.; Bouxon, B. Tetrahedron 1990, 46, 201. David, S.; Augé, C.; Gautheron, C. Adv. Carbohydr. Chem. and Biochem. 1991, 49, 175. Sparks, M. A.; Williams, K. W.; Lukacs, C.; Schnell, A.; Priebe, G.; Spaltenstein, A.; Whitesides, G. M. Tetrahedron 1993, 49, 1. Kragl, U.; Gödde, A.; Wandrey, C.; Kinzy, W.; Cappon, J. J.; Lugtenburg, J. Tetrahedron: Asymmetry 1993, 4, 1193. Kong, D. C. M.; von Itzstein, M. Tetrahedron Lett. 1995, 36, 957.
14. Uchida, Y.; Tsukada, Y.; Sugimori, T. J. Biochem. 1984, 96, 507. Augé, C.; David, S.; Gautheron, C. Tetrahedron Lett. 1984, 25, 4663. Augé, C.; Gautheron, C. J. Chem. Soc., Chem. Commun. 1987, 859. Kim, M.-J.; Hennen, W. J.; Sweers, M.; Wong, C.-H. J. Am. Chem. Soc. 1988, 110, 6481. Augé, C.; David, S.; Malleron, A. Carbohydr. Res. 1989, 188, 201. Augé, C.; Gautheron, C.; David, S.; Malleron, A.; Cavayé, B.; Bouxon, B. Tetrahedron 1990, 46, 201. David, S.; Augé, C.; Gautheron, C. Adv. Carbohydr. Chem. and Biochem. 1991, 49, 175. Sparks, M. A.; Williams, K. W.; Lukacs, C.; Schnell, A.; Priebe, G.; Spaltenstein, A.; Whitesides, G. M. Tetrahedron 1993, 49, 1. Kragl, U.; Gödde, A.; Wandrey, C.; Kinzy, W.; Cappon, J. J.; Lugtenburg, J. Tetrahedron: Asymmetry 1993, 4, 1193. Kong, D. C. M.; von Itzstein, M. Tetrahedron Lett. 1995, 36, 957.
15. For regioselective oxidation to 4-oxo Neu5Ac derivatives, see: (a) Hartmann, M.; Zbiral, E. Liebigs Ann. Chem. 1991, 795. For the synthesis of 4-substituted Neu5Ac2en derivatives via an oxazoline analogue, see: (b) von Itzstein, M.; Jin, B.; Wu, W.-Y.; Chandler, M. Carbohydr. Res. 1993, 244, 181.
16. For regioselective oxidation to 4-oxo Neu5Ac derivatives, see: (a) Hartmann, M.; Zbiral, E. Liebigs Ann. Chem. 1991, 795. For the synthesis of 4-substituted Neu5Ac2en derivatives via an oxazoline analogue, see: (b) von Itzstein, M.; Jin, B.; Wu, W.-Y.; Chandler, M. Carbohydr. Res. 1993, 244, 181.
17. Zbiral, E. Carbohydrates: Synthetic Methods and Applications in Medicinal Chemistry, Ogura, H.; Hasegawa, A.; Suami, T. Eds.; VCH Publishers: New York, 1992, Chapter 16, p 304, and references cited therein.
18. von Itzstein, M.; Wu, W.-Y.; Kok, G. B.; Pegg, M. S.; Dyason, J. C.; Jin, B.; van Phan, T.; Smythe, M. L.; White, H. F.; Oliver, S. W.; Colman, P. M.; Varghese, J. N.; Ryan, D. M.; Woods, J. M.; Bethell, R. C.; Hotham, V. G.; Cameron, J. M.; Penn, C. R. Nature 1993, 363, 48. von Itzstein, M.; Wu, W.-Y.; Jin, B. Carbohydr. Res. 1994, 259, 301.
19. von Itzstein, M.; Wu, W.-Y.; Kok, G. B.; Pegg, M. S.; Dyason, J. C.; Jin, B.; van Phan, T.; Smythe, M. L.; White, H. F.; Oliver, S. W.; Colman, P. M.; Varghese, J. N.; Ryan, D. M.; Woods, J. M.; Bethell, R. C.; Hotham, V. G.; Cameron, J. M.; Penn, C. R. Nature 1993, 363, 48. von Itzstein, M.; Wu, W.-Y.; Jin, B. Carbohydr. Res. 1994, 259, 301.
20. Dondoni, A.; Boscarato, A.; Marra, A. Tetrahedron: Asymmetry 1994, 5, 2209.
21. Kok, G. B.; Mackey, B.; von Itzstein, M. Carbohydr. Res. 1996, 289, 67.
22. Hartmann, M.; Zbiral, E. Monatsh, für Chem. 1989, 120, 899.
23. 13CNMR spectral data for compound 21 and its 4-epimer 23 are indistinguishable from those previously reported (see Ref. 11).
24. Schreiner, E.; Zbiral, E.; Kleineidam, R. G.; Schauer, R. Liebigs Ann. Chem. 1991, 129.