메뉴 건너뛰기




Volumn 3, Issue 3, 1997, Pages 424-430

Hetero-Diels-Alder reaction with thiazolyl oxabutadienes - Model studies toward the synthesis of directly linked C-disaccharides

Author keywords

asymmetric synthesis; C disaccharides; carbohydrates; hetero Diels Alder reactions; thiazolyl oxabutadienes

Indexed keywords


EID: 0030912026     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.19970030314     Document Type: Article
Times cited : (21)

References (58)
  • 1
    • 0021526965 scopus 로고
    • For monographs, see: a) W. Oppolzer, Angew. Chem. Int. Ed. Engl. 1984, 23, 876. b) G. Helmchen, R. Karge, J. Weetman in Modern Synthetic Methods, Vol. 4 (Ed.: R. Scheffold), Springer, Berlin, 1986, p. 261. c) D. L. Boger, S. N. Weinreb, Hetera-Diels - Alder Methodology in Organic Synthesis, Academic Press, London, 1987. d) W. Carruthers, Cycloaddition Reactions in Organic Synthesis, Pergamon, Oxford, 1990. e) H. Waldmann, Synthesis 1994, 535.
    • (1984) Angew. Chem. Int. Ed. Engl. , vol.23 , pp. 876
    • Oppolzer, W.1
  • 2
    • 0000233508 scopus 로고
    • Ed.: R. Scheffold, Springer, Berlin
    • For monographs, see: a) W. Oppolzer, Angew. Chem. Int. Ed. Engl. 1984, 23, 876. b) G. Helmchen, R. Karge, J. Weetman in Modern Synthetic Methods, Vol. 4 (Ed.: R. Scheffold), Springer, Berlin, 1986, p. 261. c) D. L. Boger, S. N. Weinreb, Hetera-Diels - Alder Methodology in Organic Synthesis, Academic Press, London, 1987. d) W. Carruthers, Cycloaddition Reactions in Organic Synthesis, Pergamon, Oxford, 1990. e) H. Waldmann, Synthesis 1994, 535.
    • (1986) Modern Synthetic Methods , vol.4 , pp. 261
    • Helmchen, G.1    Karge, R.2    Weetman, J.3
  • 3
    • 0003719612 scopus 로고
    • Academic Press, London
    • For monographs, see: a) W. Oppolzer, Angew. Chem. Int. Ed. Engl. 1984, 23, 876. b) G. Helmchen, R. Karge, J. Weetman in Modern Synthetic Methods, Vol. 4 (Ed.: R. Scheffold), Springer, Berlin, 1986, p. 261. c) D. L. Boger, S. N. Weinreb, Hetera-Diels - Alder Methodology in Organic Synthesis, Academic Press, London, 1987. d) W. Carruthers, Cycloaddition Reactions in Organic Synthesis, Pergamon, Oxford, 1990. e) H. Waldmann, Synthesis 1994, 535.
    • (1987) Hetera-Diels - Alder Methodology in Organic Synthesis
    • Boger, D.L.1    Weinreb, S.N.2
  • 4
    • 0003523008 scopus 로고
    • Pergamon, Oxford
    • For monographs, see: a) W. Oppolzer, Angew. Chem. Int. Ed. Engl. 1984, 23, 876. b) G. Helmchen, R. Karge, J. Weetman in Modern Synthetic Methods, Vol. 4 (Ed.: R. Scheffold), Springer, Berlin, 1986, p. 261. c) D. L. Boger, S. N. Weinreb, Hetera-Diels - Alder Methodology in Organic Synthesis, Academic Press, London, 1987. d) W. Carruthers, Cycloaddition Reactions in Organic Synthesis, Pergamon, Oxford, 1990. e) H. Waldmann, Synthesis 1994, 535.
    • (1990) Cycloaddition Reactions in Organic Synthesis
    • Carruthers, W.1
  • 5
    • 84920294058 scopus 로고
    • For monographs, see: a) W. Oppolzer, Angew. Chem. Int. Ed. Engl. 1984, 23, 876. b) G. Helmchen, R. Karge, J. Weetman in Modern Synthetic Methods, Vol. 4 (Ed.: R. Scheffold), Springer, Berlin, 1986, p. 261. c) D. L. Boger, S. N. Weinreb, Hetera-Diels - Alder Methodology in Organic Synthesis, Academic Press, London, 1987. d) W. Carruthers, Cycloaddition Reactions in Organic Synthesis, Pergamon, Oxford, 1990. e) H. Waldmann, Synthesis 1994, 535.
    • (1994) Synthesis , vol.535
    • Waldmann, H.1
  • 6
    • 0342828052 scopus 로고
    • ACS Symp. Ser. no. 494
    • For carbohydrate de novo synthesis based on inter-and intramolecular cycloaddition reactions, see: Cycloaddition Reactions in Carbohydrate Chemistry, ACS Symp. Ser. no. 494, 1992.
    • (1992) Cycloaddition Reactions in Carbohydrate Chemistry
  • 11
    • 0001001958 scopus 로고    scopus 로고
    • and previous papers of the senior author (L. F. T.)
    • d) L. F. Tietze, C. Schneider, A. Grote, Chem. Eur. J. 1996, 2, 139 and previous papers of the senior author (L. F. T.).
    • (1996) Chem. Eur. J. , vol.2 , pp. 139
    • Tietze, L.F.1    Schneider, C.2    Grote, A.3
  • 21
    • 0004231915 scopus 로고
    • CRC, Boca Raton, chapt. 8
    • For recent monographs, see: a) M. H. D. Postema, C-Glycoside Synthesis, CRC, Boca Raton, 1995, chapt. 8, p. 193. b) G. Casiraghi, F. Zanardi, G. Rassu, P. Spanu, Chem. Rev. 1995, 95, 1677. c) D. E. Levy, C. Tang, The Chemistry of C-Glycosides, Elsevier, Oxford, 1995.
    • (1995) C-Glycoside Synthesis , pp. 193
    • Postema, M.H.D.1
  • 22
    • 0001033542 scopus 로고
    • For recent monographs, see: a) M. H. D. Postema, C-Glycoside Synthesis, CRC, Boca Raton, 1995, chapt. 8, p. 193. b) G. Casiraghi, F. Zanardi, G. Rassu, P. Spanu, Chem. Rev. 1995, 95, 1677. c) D. E. Levy, C. Tang, The Chemistry of C-Glycosides, Elsevier, Oxford, 1995.
    • (1995) Chem. Rev. , vol.95 , pp. 1677
    • Casiraghi, G.1    Zanardi, F.2    Rassu, G.3    Spanu, P.4
  • 23
    • 0003522385 scopus 로고
    • Elsevier, Oxford
    • For recent monographs, see: a) M. H. D. Postema, C-Glycoside Synthesis, CRC, Boca Raton, 1995, chapt. 8, p. 193. b) G. Casiraghi, F. Zanardi, G. Rassu, P. Spanu, Chem. Rev. 1995, 95, 1677. c) D. E. Levy, C. Tang, The Chemistry of C-Glycosides, Elsevier, Oxford, 1995.
    • (1995) The Chemistry of C-Glycosides
    • Levy, D.E.1    Tang, C.2
  • 24
    • 85064651982 scopus 로고
    • 2 linkage: A. Chénedé, E. Perrin, E. D. Rekaï, P. Sinaÿ, Synlett 1994, 420. R. Ferrito, P. Vogel, Tetrahedron: Asymm. 1994, 5, 2077. L. Lay, F. Nicotra, C. Pangrazio, L. Panza, G. Russo, J. Chem. Soc. Perkin Trans 1 1994, 333.
    • (1994) Synlett , pp. 420
    • Chénedé, A.1    Perrin, E.2    Rekaï, E.D.3    Sinaÿ, P.4
  • 25
    • 0028139033 scopus 로고
    • 2 linkage: A. Chénedé, E. Perrin, E. D. Rekaï, P. Sinaÿ, Synlett 1994, 420. R. Ferrito, P. Vogel, Tetrahedron: Asymm. 1994, 5, 2077. L. Lay, F. Nicotra, C. Pangrazio, L. Panza, G. Russo, J. Chem. Soc. Perkin Trans 1 1994, 333.
    • (1994) Tetrahedron: Asymm. , vol.5 , pp. 2077
    • Ferrito, R.1    Vogel, P.2
  • 27
    • 84988137828 scopus 로고
    • b) CH(OH) linkage: H. Dietrich, R. R. Schmidt, Liebigs. Ann. Chem. 1994, 975. H. Dietrich, C. Regele-Mayer, R. R. Schmidt, Carbohydrate Lett. 1994, 1, 115.
    • (1994) Liebigs. Ann. Chem. , pp. 975
    • Dietrich, H.1    Schmidt, R.R.2
  • 29
    • 0342887458 scopus 로고
    • 2 linkage, see: O. R. Martin, W. Lai, J. Org. Chem. 1993, 58, 176. O. R. Martin, F. Xie, R. Kakarla, R. Benhamza, Synlett 1993, 165. D. Mazéas, T. Skrydstrup, O. Doumeix, J.-M. Beau, Angew. Chem. Int. Ed. Engl. 1994, 33, 1383.
    • (1993) J. Org. Chem. , vol.58 , pp. 176
    • Martin, O.R.1    Lai, W.2
  • 30
    • 84988096639 scopus 로고
    • 2 linkage, see: O. R. Martin, W. Lai, J. Org. Chem. 1993, 58, 176. O. R. Martin, F. Xie, R. Kakarla, R. Benhamza, Synlett 1993, 165. D. Mazéas, T. Skrydstrup, O. Doumeix, J.-M. Beau, Angew. Chem. Int. Ed. Engl. 1994, 33, 1383.
    • (1993) Synlett , pp. 165
    • Martin, O.R.1    Xie, F.2    Kakarla, R.3    Benhamza, R.4
  • 33
    • 0000204067 scopus 로고
    • Ed.: R. Scheffold, Verlag Helvetica Chimica Acta, Basel
    • For monographs and recent papers with leading references, see: a) A. Dondoni, in Modern Synthetic Methods, Vol. 6 (Ed.: R. Scheffold), Verlag Helvetica Chimica Acta, Basel, 1992, p. 377. b) A. Dondoni, A. Marra, in Preparative Carbohydrate Chemistry (Ed.: S. Hanessian), M. Dekker, New York, 1997, chapter 9.
    • (1992) Modern Synthetic Methods , vol.6 , pp. 377
    • Dondoni, A.1
  • 34
    • 0004288915 scopus 로고    scopus 로고
    • Ed.: S. Hanessian, M. Dekker, New York, chapter 9
    • For monographs and recent papers with leading references, see: a) A. Dondoni, in Modern Synthetic Methods, Vol. 6 (Ed.: R. Scheffold), Verlag Helvetica Chimica Acta, Basel, 1992, p. 377. b) A. Dondoni, A. Marra, in Preparative Carbohydrate Chemistry (Ed.: S. Hanessian), M. Dekker, New York, 1997, chapter 9.
    • (1997) Preparative Carbohydrate Chemistry
    • Dondoni, A.1    Marra, A.2
  • 47
    • 0028840576 scopus 로고
    • 2) to achieve rate enhancement of cycloaddition reactions. See: S. T. Handy, P. A. Grieco, C. Mineur, L. Ghosez, Synlett, 1995, 565; R. Tamion, C. Mineur, L. Ghosez, Tetrahedron Lett. 1995, 36, 8977.
    • (1995) Synlett , pp. 565
    • Handy, S.T.1    Grieco, P.A.2    Mineur, C.3    Ghosez, L.4
  • 48
    • 0028840576 scopus 로고
    • 2) to achieve rate enhancement of cycloaddition reactions. See: S. T. Handy, P. A. Grieco, C. Mineur, L. Ghosez, Synlett, 1995, 565; R. Tamion, C. Mineur, L. Ghosez, Tetrahedron Lett. 1995, 36, 8977.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 8977
    • Tamion, R.1    Mineur, C.2    Ghosez, L.3
  • 49
    • 84920294056 scopus 로고    scopus 로고
    • note
    • These reaction conditions suffered from low reproducibility, since in another experiment the ratio between 3a and 3b was 1:1.
  • 50
    • 0000045148 scopus 로고
    • Vinyl thiazoles are converted to saturated aldehydes due to the olefin reduction that takes place in the course of the thiazolyl-to-formyl deblocking sequence. See: A. Dondoni, G. Fantin, M. Fogagnolo, A. Medici, P. Pedrini, Tetrahedron 1988, 44, 2021.
    • (1988) Tetrahedron , vol.44 , pp. 2021
    • Dondoni, A.1    Fantin, G.2    Fogagnolo, M.3    Medici, A.4    Pedrini, P.5
  • 53
    • 85086809368 scopus 로고    scopus 로고
    • note
    • 2.
  • 54
    • 85086809652 scopus 로고    scopus 로고
    • note
    • eq J = 6.0 Hz.
  • 56
    • 85086809089 scopus 로고    scopus 로고
    • note
    • ax/H-3 J = 12.7 Hz, H-3/H-4 J = 9.1 Hz, H-4/H-5 J = 9.4 Hz.
  • 57
    • 0004200720 scopus 로고
    • Wiley, New York
    • The facile anomerization of 15 as well as of 11a and 12a, or their products, is very likely due to acid catalysis by silica gel or traces of acetic acid contained in acetonitrile. This enhanced reactivity at the anomeric center is typical of 2-deoxy sugars. See: P. M. Collins, R. J. Ferrier, Monosaccharides, Wiley, New York, 1995, pp. 73 and 217.
    • (1995) Monosaccharides , pp. 73
    • Collins, P.M.1    Ferrier, R.J.2
  • 58
    • 85086809324 scopus 로고    scopus 로고
    • note
    • eq J = 6.3 Hz.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.