The first synthesis of a ribo-hexos-5-ulose: The l-enantiomer

Journal of Carbohydrate Chemistry

Volumn 18, Issue 9, 1999, Pages 1037-1049

  Barili, Pier Luigi ^a   Bergonzi, Maria Camilla ^a   Berti, Giancarlo ^a   Catelani, Giorgio ^a   D'Andrea, Felicia ^a   De Rensis, Francesco ^a  

^a UNIVERSITY OF PISA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0033427226     PISSN: 07328303     EISSN: None     Source Type: Journal    
DOI: 10.1080/07328309908544053     Document Type: Article

References (23)

1. Part 10 of the series, " Rare and Complex Saccharides from D-galactose and other Milk-derived Carbohydrates". For part 9 see ref. 4c.
2. D. E. Kiely and H. G. Fletcher Jr., J. Am. Chem. Soc, 90, 3289 (1968);
3. D. E. Kiely and H. G. Fletcher, J. Org. Chem., 34, 1386 (1969).
4. J. M. Riordan, P. E. Morris, Jr. and D. E. Kiely, J. Carbohydr. Chem., 12, 865 (1993);
5. D. E. Kiely, R. E. Harry-O'Kuru, P. E. Morris, Jr., D. W. Morton and J. M. Riordan, J. Carbohydr. Chem., 16, 1159 (1997).
6. P. L. Barili, G. Berti, G. Catelani and F. D'Andrea, Gazz. Chim. Ital., 122, 135 (1992);
7. P. L. Barili, G. Berti, G. Catelani, F. D'Andrea and F. De Rensis, Tetrahedron, 53, 8665 (1997);
8. P. L. Barili, G. Berti, G. Catelani, F. D'Andrea, F. De Rensis and G. Goracci, J. Carbohydr. Chem., 17, 1167 (1998).
9. E. W. Baxter and A. B. Reitz, J. Org. Chem., 59, 3175 (1994);
10. P. L. Barili, G. Berti, G. Catelani, F. D'Andrea, F. De Rensis and L. Puccioni, Tetrahedron, 53, 3407 (1997).
11. M. Adinolfi, G. Barone, A. Iadonisi and L. Mangoni, Tetrahedron Lett., 39, 2021 (1998).
12. An alternative name of 3, according to the more recent rules could be methyl (5R)-5-methoxy-α-L-arabino-hexopyranoside.
13. P. L. Barili, G. Berti, G. Catelani and F. D'Andrea, Carbohydr. Res., 190, 13 (1989).
14. P. L. Barili, G. Berti, G. Catelani, F. Colonna and A. Marra, Tetrahedron Lett., 27, 2307 (1986).
15. M. C. Bergonzi, G. Catelani, F. D'Andrea and F. De Rensis, Carbohydr. Res., 311, 231 (1998).
16. E. J. Corey and A. Venkateswarlu, J. Am. Chem. Soc., 94, 6190 (1972).
17. S. K. Chaudhary and O. Hernandez, Tetrahedron Lett., 2, 99 (1979).
18. P. L. Barili, G. Catelani, F. D'Andrea and E. Mastrorilli, J. Carbohydr. Chem., 16, 1001 (1997).
19. A. Levy, H. M. Flowers and N. Sharon, Carbohydr. Res., 4, 305 (1967).
20. S. V. Ley, J. Norman, W. P. Griffith and S. P. Marsden, Synthesis, 639 (1994).
21. PC MODEL, Serena Software, P.O. Box 3076, Bloomington, IN 47402, USA, (1990).
22. F. W. Lichtenthaler, E. Kaji and S. Weprek, J. Org. Chem, 50, 3505 (1985).
23. M. Bessodes, J. Shamsazar and K. Antonakis, Synthesis, 7, 560 (1988).