Synthesis of C-disaccharides from C-formyl glycosides

Tetrahedron Letters

Volumn 37, Issue 42, 1996, Pages 7587-7590

  Dondoni, Alessandro ^a   Boscarato, Alessia ^a   Zuurmond, Helene ^a  

^a UNIVERSITY OF FERRARA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

DISACCHARIDE;

ARTICLE; CARBOHYDRATE SYNTHESIS; CHIRALITY; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY; TECHNIQUE;

EID: 0030583504     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01667-X     Document Type: Article

References (20)

1. 1. Rouzaud, D.; Sinaÿ, P., J. Chem. Soc., Chem. Commun., 1983, 1353. Martin, O. R., Lai, W., J. Org. Chem. 1993, 58, 176. Mallet, A.; Mallet, J.-M.; Sinaÿ, P., Tetrahedron Asymmetry, 1994, 5, 2593. Dietrich, H.; Schmidt, R.R., Liebigs Ann. Chem., 1994, 975. Wei, A.; Haudrechy, A.; Audin, C.; Hyuk-Sang, J.; Haudrechy-Bretel, N. ; Kishi, Y., J. Org. Chem., 1995, 60, 2160. Streiche, H.; Geyer, A.; Schmidt, R. R., Chem. Eur. J., 1996, 2, 502.
2. Rouzaud, D.; Sinaÿ, P., J. Chem. Soc., Chem. Commun., 1983, 1353. Martin, O. R., Lai, W., J. Org. Chem. 1993, 58, 176. Mallet, A.; Mallet, J.-M.; Sinaÿ, P., Tetrahedron Asymmetry, 1994, 5, 2593. Dietrich, H.; Schmidt, R.R., Liebigs Ann. Chem., 1994, 975. Wei, A.; Haudrechy, A.; Audin, C.; Hyuk-Sang, J.; Haudrechy-Bretel, N. ; Kishi, Y., J. Org. Chem., 1995, 60, 2160. Streiche, H.; Geyer, A.; Schmidt, R. R., Chem. Eur. J., 1996, 2, 502.
3. Rouzaud, D.; Sinaÿ, P., J. Chem. Soc., Chem. Commun., 1983, 1353. Martin, O. R., Lai, W., J. Org. Chem. 1993, 58, 176. Mallet, A.; Mallet, J.-M.; Sinaÿ, P., Tetrahedron Asymmetry, 1994, 5, 2593. Dietrich, H.; Schmidt, R.R., Liebigs Ann. Chem., 1994, 975. Wei, A.; Haudrechy, A.; Audin, C.; Hyuk-Sang, J.; Haudrechy-Bretel, N. ; Kishi, Y., J. Org. Chem., 1995, 60, 2160. Streiche, H.; Geyer, A.; Schmidt, R. R., Chem. Eur. J., 1996, 2, 502.
4. Rouzaud, D.; Sinaÿ, P., J. Chem. Soc., Chem. Commun., 1983, 1353. Martin, O. R., Lai, W., J. Org. Chem. 1993, 58, 176. Mallet, A.; Mallet, J.-M.; Sinaÿ, P., Tetrahedron Asymmetry, 1994, 5, 2593. Dietrich, H.; Schmidt, R.R., Liebigs Ann. Chem., 1994, 975. Wei, A.; Haudrechy, A.; Audin, C.; Hyuk-Sang, J.; Haudrechy-Bretel, N. ; Kishi, Y., J. Org. Chem., 1995, 60, 2160. Streiche, H.; Geyer, A.; Schmidt, R. R., Chem. Eur. J., 1996, 2, 502.
5. Rouzaud, D.; Sinaÿ, P., J. Chem. Soc., Chem. Commun., 1983, 1353. Martin, O. R., Lai, W., J. Org. Chem. 1993, 58, 176. Mallet, A.; Mallet, J.-M.; Sinaÿ, P., Tetrahedron Asymmetry, 1994, 5, 2593. Dietrich, H.; Schmidt, R.R., Liebigs Ann. Chem., 1994, 975. Wei, A.; Haudrechy, A.; Audin, C.; Hyuk-Sang, J.; Haudrechy-Bretel, N. ; Kishi, Y., J. Org. Chem., 1995, 60, 2160. Streiche, H.; Geyer, A.; Schmidt, R. R., Chem. Eur. J., 1996, 2, 502.
6. Rouzaud, D.; Sinaÿ, P., J. Chem. Soc., Chem. Commun., 1983, 1353. Martin, O. R., Lai, W., J. Org. Chem. 1993, 58, 176. Mallet, A.; Mallet, J.-M.; Sinaÿ, P., Tetrahedron Asymmetry, 1994, 5, 2593. Dietrich, H.; Schmidt, R.R., Liebigs Ann. Chem., 1994, 975. Wei, A.; Haudrechy, A.; Audin, C.; Hyuk-Sang, J.; Haudrechy-Bretel, N. ; Kishi, Y., J. Org. Chem., 1995, 60, 2160. Streiche, H.; Geyer, A.; Schmidt, R. R., Chem. Eur. J., 1996, 2, 502.
7. 2. Postema, M. H. D., C-Glycoside Synthesis, CRC Press, Boca Raton, 1995. Levy, D. E.; Tang, C., The Chemistry of C-Glycosides, Elsevier, Oxford, 1995.
8. Postema, M. H. D., C-Glycoside Synthesis, CRC Press, Boca Raton, 1995. Levy, D. E.; Tang, C., The Chemistry of C-Glycosides, Elsevier, Oxford, 1995.
9. 3. Wang, Y.; Goekjian, P. G.; Ryckman, D. M.; Miller, W. H.; Babirad, S. A.; Kishi, Y., J. Org. Chem. 1992, 57, 482.
10. 4. Evidence has been recently provided against the generality of the conformational similarity between O-and C-glycosides. See, Espinosa, J.-F.; Cañada, F. J.; Asensio, J. L.; Dietrich, H.; Martín-Lomas, M.; Schmidt, R. R.; Jiménez-Barbero, J., Angew. Chem. Int. Ed. Engl., 1996, 35, 303.
11. 5. Dondoni, A.; Scherrmann, M.-C., J. Org. Chem., 1994, 59, 6404.
12. 6. Secrist III, J. A.; Wu, S.-R., J. Org. Chem., 1979, 44, 1434.
13. 7. Aldehydes 1 and 2 were liberated from the corresponding thiazole precursor as described (ref. 5) and purified by rapid chromatography over a short column of silica gel (ethyl acetate-cyclohexane 2:1 for aldehyde 1 and ethyl acetate-cyclohexane 1:1 for aldehyde 2). These compounds form hydrates.
14. 6,5 5.7 Hz).
15. 3), M+Na 443.
16. 10. Dondoni, A.; Scherrmann, M.-C, Tetrahedron Lett., 1993, 34, 7319.
17. 11. Kobertz, W. R.; Bertozzi, C. R.; Bednarski, M. D., J. Org. Chem., 1996, 61, 1894.
18. 12. The unoptimized low yield was justified by an unusual and extraordinary event: closure of the laboratory! (see ref. 11).
19. 13. Removal of the isopropylidene groups with 80% acetic acid at reflux temperature for 1/2 h gave 9 as a mixture of furanose and pyranose forms in 87% yield.
20. 3OD): δ 28.0, 29.2 (C-6, C-7), 94.1 (C-1α), 98.6 (C-1β).