An efficient catalysed ceric ammonium nitrate acetonation method for carbohydrates

Synlett

Volumn , Issue 6, 2000, Pages 887-889

  Manzo, Emiliano ^a   Barone, Gaspare ^a   Parrilli, Michelangelo ^a  

^a UNIVERSITY OF NAPLES FEDERICO II   (Italy)

Author keywords

Acetals; Acetonation; Carbohydrates; Ceric ammonium nitrate; Lanthanides

Indexed keywords

ACETAL DERIVATIVE; ACETONE; ACETONIDE; CERIC AMMONIUM NITRATE; CERIUM; DIMETHOXYPROPANE; MONOSACCHARIDE; N,N DIMETHYLFORMAMIDE; OLIGOSACCHARIDE; SUCROSE; UNCLASSIFIED DRUG;

ARTICLE; CARBOHYDRATE SYNTHESIS; CATALYSIS; CATALYST; REACTION TIME; TEMPERATURE;

EID: 0034084327     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (28)

1. (a) Ho, T.-L. Organic Syntheses by Oxidation with Metal Compounds, Plenum Press, New York, 1986: p. 569.
2. (b) Ho, T.-L. In Encyclopaedia of Reagents for Organic Synthesis; Paquette, L. A., Ed., John Wiley, New York, 1995; p. 1025.
3. Molander, G. A. Chem. Rev. 1992, 92, 29.
4. (a) Ates, A.; Gautier, A.; Bern, L.; Plancher, J.-M.; Quesnel, Y.; Markó, I. Tetrahedron Lett. 1999, 40, 1799.
5. (b) Markó, I; Ates, A.; Gautier, A.; Bern, L.; Plancher, J.-M.; Quesnel, Y.; Vanherck, J-C. Angew. Chem. Int. Ed. Engl. 1999, 38, 3207.
6. (a) DeBelder, A. N. Adv. Carbohydr. Chem. Biochem. 1977, 34, 179.
7. (b) Collins, P. N.; Ferrier, R. J. Monosaccharides, John Wiley, New York, 1995; p.389.
8. Calinoud, P.; Gelas, J. in Preparative Carbohydrate Chemistry, Hanessian, S. (Ed.) Marcel Dekker, New York, 1997; p. 3.
9. (a) Clode, M. D. Chem. Rev. 1979, 79, 491.
10. (b) Rauter, A. P.; Ramôa-Ribeiro, F.; Fernandes, A. C.; Figueiredo, J. A. Tetrahedron 1995, 51, 6529.
11. Asakura, J.; Matsubara, Y.; Yoshihara, M. J. Carbohydr. Chem. 1996, 15, 231.
12. (a) Hasegawa, A.; Fletcher Jr, H. G. Carbohydr. Res. 1973, 29, 209.
13. (b) Khan, R.; Mufti, K. S. Carbohydr. Res. 1975, 43, 247.
14. Khan, R.; Mufti, K. S.; Jenner, M. R. Carbohydr. Res. 1978, 65, 109.
15. Fanton, E.; Gelas, J.; Horton, D. J. Org. Chem. 1981, 46, 4057
16. Fanton, E.; Gelas, J.; Horton, J. Chem. Soc. Chem. Commun. 1980, 21.
17. Ueno, Y.; Hori, K.; Yamauchi, R.; Kiso, M.; Hasegawa, A.; Kato, K. Carbohydr. Res. 1981, 89, 271.
18. Baer, H. H.; Abbas, S. A. Carbohydr. Res. 1979, 77, 117.
19. Wolfrom, M. L.; Diwadkar, A. B.; Gelas, J.; Horton, D. Carbohydr. Res. 1974, 35, 87.
20. Kiso, M.; Hasekawa, A. Carbohydr. Res. 1976, 52, 87.
21. Gelas, J.; Horton, D. Carbohydr. Res. 1978, 67, 371.
22. Gelas, J.; Horton, D. Carbohydr. Res. 1975, 45, 181.
23. 3 s δ 1.67, methyls of isopropylidene group: δ 1.43 and 1.31; methoxytrityl group: OCH3 δ 3.29 (x 2), aromatic signals δ 6.7-7.7, respectively.
24. In this case, the only difference with the above conditions was the use of a larger amount of DMP (4.38 mmol, 552 μL). This quantity was added in different aliquots during the reaction, namely, at beginning 2.19 mmol (276 μL), 1.09 mmol (138 μL) after 16 h and other 1.09 mmol (138 μL) at 19 h. Work up as above.
25. sec ref. 3b p. 356
26. Mino, G.; Kaizerman, S.; Rasmussen, E. J. Chem. Soc. 1959, 1494.
27. Markó, I; Ates, A.; Benoît, A.; Gautier, A.; Quesnet, Y.;Turet, L.; Wiaux, M. Tetrahedron Lett. 1999, 40, 5613.
28. 3, then the organic phase was evaporated and chromatographed as mentioned above.