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Volumn 5, Issue 12, 1999, Pages 3562-3572

Stereoselective conjugate addition of nitrogen and carbon nucleophiles to sugar-derived enones: Synthesis of sialic acid analogues

Author keywords

Azides; Carbohydrate mimetics; Michael additions; Neuraminic acids; Sialic acids

Indexed keywords

MANNOSE; SIALIC ACID DERIVATIVE;

EID: 0032805122     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1521-3765(19991203)5:12<3562::aid-chem3562>3.3.co;2-n     Document Type: Article
Times cited : (29)

References (67)
  • 2
    • 0025818102 scopus 로고
    • For an alternative route via aldol condensation of the lithium enolate of 2-acetylthiazole as an equivalent of the pyruvate anion, see: A. Dondoni, P. Merino, J. Org. Chem. 1991, 56, 5294-5301. The same synthetic approach has been recently extended by others to the preparation of analogues of Neu5Ac [ref. 7f] while the relevant reference to the our earlier work was omitted.
    • (1991) J. Org. Chem. , vol.56 , pp. 5294-5301
    • Dondoni, A.1    Merino, P.2
  • 4
    • 0001276617 scopus 로고
    • Sialic acids. Chemistry, metabolism, and function
    • Springer Verlag, Wien
    • Sialic Acids. Chemistry, Metabolism, and Function in Cell Biology Monographs (Ed.: R. Schauer), Springer Verlag, Wien, 1982.
    • (1982) Cell Biology Monographs
    • Schauer, R.1
  • 6
    • 0026445723 scopus 로고
    • For recent reviews on the biological roles of sialic acids, see: a) L. A. Lasky, Science 1992, 258, 964-969;
    • (1992) Science , vol.258 , pp. 964-969
    • Lasky, L.A.1
  • 9
    • 0000525695 scopus 로고
    • d) A. Giannis, Angew. Chem. 1994, 106, 188-191; Angew. Chem. Int. Ed. Engl. 1994, 33, 178-180;
    • (1994) Angew. Chem. , vol.106 , pp. 188-191
    • Giannis, A.1
  • 10
    • 0028121730 scopus 로고
    • d) A. Giannis, Angew. Chem. 1994, 106, 188-191; Angew. Chem. Int. Ed. Engl. 1994, 33, 178-180;
    • (1994) Angew. Chem. Int. Ed. Engl. , vol.33 , pp. 178-180
  • 12
    • 0001094662 scopus 로고    scopus 로고
    • f) R. A. Dwek, Chem. Rev. 1996, 96, 683-720.
    • (1996) Chem. Rev. , vol.96 , pp. 683-720
    • Dwek, R.A.1
  • 19
    • 0027082554 scopus 로고
    • The synthesis of 5-acetamidomethyl-3,5-dideoxy-nonulosonic acid derivative, a homologue of Neu5Ac (1), has been reported: K. Koppert, R. Brossmer, Tetrahedron Lett. 1992, 33, 8031-8034.
    • (1992) Tetrahedron Lett. , vol.33 , pp. 8031-8034
    • Koppert, K.1    Brossmer, R.2
  • 27
    • 0042960761 scopus 로고
    • Metal amides, selected references, see: a) J. M. Hawkins, G. C. Fu, J. Org. Chem. 1986, 51, 2820-2822;
    • (1986) J. Org. Chem. , vol.51 , pp. 2820-2822
    • Hawkins, J.M.1    Fu, G.C.2
  • 36
    • 33748232894 scopus 로고
    • i) D. Enders, H. Wahl, W. Bettray, Angew. Chem. 1995, 107, 527-529; Angew. Chem. Int. Ed. Engl. 1995, 34, 455-457;
    • (1995) Angew. Chem. Int. Ed. Engl. , vol.34 , pp. 455-457
  • 38
    • 85050326125 scopus 로고
    • Stereochemistry of the base-promoted Michael addition reactions
    • (Eds.: E. L. Eliel, S. H. Wilen), Wiley, New York
    • Monographs; a) D. A. Oare, C. H. Heathcock, Stereochemistry of the Base-Promoted Michael Addition Reactions in Topics in Stereo-chemistry (Eds.: E. L. Eliel, S. H. Wilen), Wiley, New York, 1989, pp. 227-407;
    • (1989) Topics in Stereo-chemistry , pp. 227-407
    • Oare, D.A.1    Heathcock, C.H.2
  • 40
    • 0003280270 scopus 로고
    • Conjugate addition reactions in organic synthesis
    • (Eds.: J. E. Baldwin, P. D. Magnus), Pergamon, Oxford
    • c) P. Perlmutter, Conjugate Addition Reactions in Organic Synthesis, In Tetrahedron Organic Chemistry Series, Vol. 9 (Eds.: J. E. Baldwin, P. D. Magnus), Pergamon, Oxford, 1992;
    • (1992) Tetrahedron Organic Chemistry Series , vol.9
    • Perlmutter, P.1
  • 43
    • 85088281338 scopus 로고    scopus 로고
    • note
    • 2). At - 70°C the reaction proceeded with a good level of selectivity (ca. 9:1) up to completion but the product ratio changed to a constant 1:1 value on standing at room temperature for 16 hours.
  • 44
    • 0348249080 scopus 로고    scopus 로고
    • note
    • In general the NMR spectra at room temperature of compounds containing an N,N-dialkyl-N-Boc amine function show a double set of signals arising from the hindered rotation around the σ-bonds. Hence the spectrum of a mixture of epimers can be rather complex due to the presence of the corresponding rotamers. At higher temperatures (120-160°C) the spectra become simpler because of the coalescence of signals.
  • 45
    • 0346988319 scopus 로고    scopus 로고
    • note
    • The α-D anomeric configuration of 9a and 13, and the β-D configuration of 9b were supported by a substantial NOE between the methoxy group and H-5ax.
  • 46
    • 0032447309 scopus 로고    scopus 로고
    • For a recent account on methods and synthetic applications based on the thiazole-aldehyde equivalence, see: A. Dondoni, Synthesis 1998, 1681-1706.
    • (1998) Synthesis , pp. 1681-1706
    • Dondoni, A.1
  • 48
    • 0348249079 scopus 로고    scopus 로고
    • note
    • It is worth recalling here that the direct conversion of the thiazole ring into the carboxylate group has been found so far to be unpractical as a result of low yields and harsh conditions, see [ret. 1].
  • 49
    • 0346988318 scopus 로고    scopus 로고
    • note
    • This N-protective group arrangement was proved to be crucial in various thiazole-based syntheses, see [ref. 5].
  • 50
    • 0001795660 scopus 로고
    • Various transition state models, some of which empirical [ref. 11a], other based on molecular mechanics: A. Bernardi, A. M. Capelli, C. Gennari, C. Scolastico, Tetrahedron: Asymmetry 1990, 1, 21-32 and molecular orbital studies: A. E. Dorigo, K. Morokuma, J. Am. Chem. Soc. 1989, 111, 6524-6536 have been proposed to account for the variable stereochemical outcome of Michael-type reactions.
    • (1990) Tetrahedron: Asymmetry , vol.1 , pp. 21-32
    • Bernardi, A.1    Capelli, A.M.2    Gennari, C.3    Scolastico, C.4
  • 51
    • 0000449145 scopus 로고
    • Various transition state models, some of which empirical [ref. 11a], other based on molecular mechanics: A. Bernardi, A. M. Capelli, C. Gennari, C. Scolastico, Tetrahedron: Asymmetry 1990, 1, 21-32 and molecular orbital studies: A. E. Dorigo, K. Morokuma, J. Am. Chem. Soc. 1989, 111, 6524-6536 have been proposed to account for the variable stereochemical outcome of Michael-type reactions.
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 6524-6536
    • Dorigo, A.E.1    Morokuma, K.2
  • 55
    • 0346988317 scopus 로고    scopus 로고
    • note
    • Compound 3 was contaminated by ca. 10% of unreacted Me-3 which could not be removed by chromatography. An alternative synthesis of this compound has been recently reported by others [ref. 7e].
  • 56
    • 85088280363 scopus 로고    scopus 로고
    • note
    • 3 to 5 and 6 were essentially unselective.
  • 63
    • 0346988316 scopus 로고    scopus 로고
    • note
    • The anomeric configuration was proved by NOE experiments.
  • 64
    • 0347583459 scopus 로고    scopus 로고
    • note
    • The incorporation of protective groups under basic conditions was not compatible with the nitromethyl group. Benzylation under acidic conditions and acetonation was unsuccessful.
  • 65
    • 0028834594 scopus 로고
    • Very likely the N-methylation of the thiazole ring was accompanied by the formation of an unstable methyl imidate function from the acetamido group at C-4. On the other hand the thiazole-to-formyl deblocking protocol is fully compatible with the presence of a NHBoc group, see [ref. 16] and A. Dondoni, D. Perrone, P. Merino, J. Org. Chem. 1995, 60, 8074-8080.
    • (1995) J. Org. Chem. , vol.60 , pp. 8074-8080
    • Dondoni, A.1    Perrone, D.2    Merino, P.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.