The assembly of carbon-linked calixarene-carbohydrate structures (C- calixsugars) by multiple Wittig olefination

Tetrahedron Letters

Volumn 38, Issue 44, 1997, Pages 7801-7804

  Dondoni, Alessandro ^a   Kleban, Martin ^a   Marra, Alberto ^a  

^a UNIVERSITY OF FERRARA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CALIXARENE; CARBOHYDRATE DERIVATIVE;

ARTICLE; CARBOHYDRATE ANALYSIS; REACTION ANALYSIS; SYNTHESIS;

EID: 0030710979     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10041-7     Document Type: Article

References (17)

1. (a) Gutsche, C. D. Calixarenes, Stoddart, J. F. Ed.; Royal Society of Chemistry; London, 1989;
2. (b) Boehmer, V., Angew. Chem., Int. Ed. Engl. 1995, 34, 713.
3. (a) Marra, A.; Scherrmann, M-C.; Dondoni, A.; Casnati, A.; Minari, P.; Ungaro, R., Angew. Chem., Int. Ed. Engl. 1994, 33, 2479;
4. (b) Marra, A.; Dondoni, A.; Sansone, F., J. Org. Chem. 1996, 61, 5155;
5. (c) Dondoni, A.; Marra, A.; Scherrmann, M-C.; Casnati, A.; Sansone, F.; Ungaro, R., Chemistry Eur J. 1997, in press.
6. For a definition of the trivial name 'calixsugar', see ref. 2b.
7. (a) Secrist III, J. A.; Wu, S.-R., J. Org. Chem., 1979, 44, 1434;
8. (b) Secrist III, J. A.; Wu, S.-R. J. Org. Chem., 1977, 42, 4084.
9. (a) Dondoni, A.; Boscarato, A.; Zuurmond, H. M., Tetrahedron Lett. 1996, 37, 7587;
10. (b) Dondoni, A; Zuurmond, H. M.; Boscarato A., J. Org. Chem. 1997, in press.
11. 3N). A byproduct of the Wittig olefination was the sugar diphenylphosphine oxide derivative.
12. MALDI-TOF mass spectra were acquired using α-cyano-4-hydroxycinnamic acid as the matrix.
13. 2Ar), 4.56 (dd, 4 H, H-3), 5.52 (d, 4 H, H-1), 6.40 and 6.44 (2 s, 8 H, arom.). The compound showed C4 symmetry, i.e. only one set of signals for all four carbohydrate moieties.
14. 4,5 = 1.7 Hz).
15. 3,4 = 3.2 Hz, 4 H, H-3), 4.85 (s, 4 H, H-1), 6.43 and 6.44 (2 s, 8 H, arom.).
16. 3,4 of compounds 3, 6a, and 7a are in agreement with literature values for 2,3-isopropylidene furanosides, i.e. < 0.5 Hz for methyl-2,3-isopropylidene-ribo-β-D-furanosides with different substituents at C-5 and 3.3 Hz for methyl-5-O-benzyl-2,3-isopropylidene-α-D-lyxo-furanoside. See : Leonard, N. J.; Carraway, K. L., J. Heterocycl. Chem. 1966, 3, 485. Taniguchi, M.; Koga, K.; Yamada, S., Tetrahedron 1974, 30, 3547.
17. 3,4 of compounds 3, 6a, and 7a are in agreement with literature values for 2,3-isopropylidene furanosides, i.e. < 0.5 Hz for methyl-2,3-isopropylidene-ribo-β-D-furanosides with different substituents at C-5 and 3.3 Hz for methyl-5-O-benzyl-2,3-isopropylidene-α-D-lyxo-furanoside. See : Leonard, N. J.; Carraway, K. L., J. Heterocycl. Chem. 1966, 3, 485. Taniguchi, M.; Koga, K.; Yamada, S., Tetrahedron 1974, 30, 3547.