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28644441564
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Nucleoside analogues with an extra heteroatom in the sugar ring (e.g., lamivudine or dioxolane-T) exhibited remarkable antiviral and anticancer activity. See Ref. 3.
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0032554269
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For examples of the equivalence between the dioxolane ring and the hydroxymethyl group applied to isoxazolidinyl nucleosides, see: P. Merino, S. Franco, N. Garces, F.L. Merchan, and T. Tejero Chem. Commun. 1998 493 494
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P. Merino, E.M. Alamo, S. Franco, F.L. Merchan, S. Simon, and T. Tejero Tetrahedron: Asymmetry 11 2000 1543 1554 see also Ref. 8b
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1842431662
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U. Chiacchio, A. Corsaro, D. Iannazzo, A. Piperno, V. Pistará, A. Rescifina, R. Romeo, G. Sindona, and G. Romeo Tetrahedron: Asymmetry 14 2003 2717 2723
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Romeo, R.7
Sindona, G.8
Romeo, G.9
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37
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28644435623
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note
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The authors have deposited the atomic coordinates for this structure with the Cambridge Crystallographic Data Centre. The coordinates can be obtained on request from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK. The graphic view showed in Figure 2 was made with ortep3 software. Copyright by Farrugia, L. J., University of Glasgow. 1997-2000.
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Change of the solvent of the reaction did not change substantially the observed ratios.
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39
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28644447078
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See Ref. 8b and references cited therein.
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See Ref. 8b and references cited therein.
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41
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0000189651
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Geometry optimizations were carried out by using the B3LYP (Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
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(1993)
J. Chem. Phys.
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Becke, A.D.1
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43
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0345491105
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Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789.) functional with the 6-31G(d) basis set. Structures were fully optimized through step by step calculations at the B3LYP/6-31G(d) level of theory and then single point calculations were performed at MP2/6-31G(d) level. All transition structures were found to have only one negative eigenvalue with the corresponding eigenvector involving the formation of the newly created C-C and C-O bonds. Vibrational frequencies were calculated (1 atm, 298.15 K) for all B3LYP/6-31G(d) optimized structures and used unscaled, to compute ZPVE and activation energies. All calculations were performed using the Gaussian 03 revision B.01 suite of programs.
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(1988)
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Lee, C.1
Yang, W.2
Parr, R.G.3
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28644447841
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(Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.;).
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(Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; and Pople, J. A.; Gaussian, Pittsburgh PA, 2003).
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Rescifina, A.4
Iannazzo, D.5
Piperno, A.6
Romeo, G.7
Romeo, R.8
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50
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28644441219
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note
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Interestingly, the (5S)-configuration of the major adducts is opposite to that found by Vasella (see Ref. 16) for the cycloaddition between N-ribosyl-C-(alkoxymethyl) nitrones and methyl methacrylate, thus pointing out the influence in the diastereofacial selectivity of the reaction not only of the chiral auxiliary but also of the dipolarophile's nature.
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Attempts of deprotecting the N-benzyl group included hydrogenation under mild conditions and reduction with Na and Li in liquid ammonia. A less common method, such as Montmorillonite K-10, which had successfully been used by us with other N-benzyl isoxazolidinyl nucleosides (see Ref. 8c) was also tested. In all cases complex reaction mixtures were obtained.
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Furthermore, the use of different N-glycosyl units, such as mannosyl, gulosyl, or erythrosyl derivatives, which are available in both enantiomeric forms, could provide access to both enantiomeric series. For representative examples of the use of those nitrones, see: K. Kasahara, H. Iida, and C. Kibayashi J. Org. Chem. 54 1989 2225 2233
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S. Cicchi, M. Marradi, M. Corsi, C. Faggi, and A. Goti Eur. J. Chem. 2003 4152 4160 see also Ref. 16
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Cicchi, S.1
Marradi, M.2
Corsi, M.3
Faggi, C.4
Goti, A.5
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