DDQ-Mediated Regioselective de-Omikron-Benzylation of Pyranosides Stilted by a 4,6-O-(2-Phenylsulfonyl)ethylidene (PSE) Clip

• Autorzy: Cabianca E. , Tatibouet A. , Rollin P.
• Języki publikacji: EN

Abstrakty

EN

A model study on diverse 4,6-acetalated O-benzylated D-glucopyranosides was performed to evaluate DDQ-mediated regioselective de-O-benzylation in connection with structural rigidity.

Słowa kluczowe

EN

PSE acetals; benzyl ethers; DDQ; regioselective deprotection

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2005
• Tom: Vol. 79 / nr 2
• Strony: 317--322
• Opis fizyczny: Bibliogr. poz. 18, rys.

Twórcy

autor

Cabianca E.

• ICOA - UMR 6005, Université d'Orléans, B.P. 6759, F-45067 Orléans, France
• Dipartimento di Chimica, Universita Ca’Foscari di Venezia, Dorsoduro 2137, I-30123 Venezia, Italy

autor

Tatibouet A.

• ICOA - UMR 6005, Université d'Orléans, B.P. 6759, F-45067 Orléans, France

autor

Rollin P.

• ICOA - UMR 6005, Université d'Orléans, B.P. 6759, F-45067 Orléans, France

Bibliografia

• 1. Stanék J., Jr., Topics Cum Chem., 154, 227 (1990).
• 2. Falck J.R., Barma D.K., Venkataraman S.K., Baati R. and Mioskowski C., Tetrahedron Lett., 43, 963' (2002) and references cited.
• 3. a) Beaupere D., Boutbaiba I., Wadouachi A., Fréchou C., Demailly G. and Uzan R., New J. Chem., 16,405 (1992); b) Ikemoto N. and Schreiber S.L., J. Am. Chem. Soc., 114, 2524 (1992).
• 4. Xia J ., Abbas S.A., Locke R.D., Piskorz C.F., Aldefer J.L. and Matta K.L., Tetrahedron Lett., 41, 169 (2000).
• 5. Plante O.J., Buchwald S.L. and Seeberger P.H., J. Am. Chem. Soc., 122, 7148 (2000).
• 6. Horita K., Yoshioka T., Tanaka T., Oikawa Y. and Yonemitsu 0., Tetrahedron, 42, 3021 (1986). 7. a) Chéry F., Rollin P., De Lucehi O. and Cossu S., Synthesis, 286 (2001); b) Rollin P. and Tatibouét A.,In “Encyclopedia of Reagents for Organic Synthesis ", Wiley & Sons, in press.
• 8. Jarowicki K. and Kocienski P., J Chem. Soc., Perkin Trans. I, 2109 (2001).
• 9. Cabianca E., Tatibouét A., De Lucchi O. and Rollin P., unpublished results. M
• 10. Greene T.W. and Wuts P.G.M., In “Protective groups in organic synthesis", 3 Ed., John Wiley & Sons,New York, pp. 79-93 (1999).
• 11. Montanari F., Gan. Chim. Ital., 86, 420 (1956).
• 12. De Lucchi O., Lucchini V., Pasquato L. and Modena G., J. Org. Chem., 49, 596 (1984).
• 13. Bako P., Bajor Z. and Laszlo T., J. Chem. Soc., Perkin Trans. 1, 3651 (1999).
• 14. a) Vedejs E., Buchanan R.A. and Watanabe Y., J. Am. Chem. Soc., 111, 8430 (1989); b) Tanaka T.,Oikawa Y., Nakajima N., 1-Iamada T. and Yonemitsu 0., Chem. Pharm. Bull., 35, 2203 (1987).
• 15. Barrett A.G.M., Read R.W. and Barton D.H.R., J. Chem. Soc., Perkin Trans. 1, 2184 (1980).
• 16. Kovac P. and Glaudemans C.P.J., J Carbohydr: Chem., 7, 317 (1988).
• 17. Chevalier-du Roizel B., Cabianca E., Rollin P. and Sinaji P., Tetrahedron, 58, 9579 (2002).
• 18. Montanari F., Gazz. Chim. Ital, 86, 428 (1956).