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Original Articles

Flexible Synthesis of Polyhydroxylated 2,2-Disubstituted Pyrrolidines

Pages 647-652 | Published online: 07 Mar 2008

REFERENCES AND NOTES

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  • To the best of our knowledge these systems represent a formerly unknown class of iminosugars. Similar structures are the corresponding γ-lactames and saturated 2,2-disubstituted pyrrolidine derivatives, see for example: a) Kuciak R. Sas W. , Tetrahedron Lett. , 35 , 8647 ( 1994 ); b) Y. Kishida, A. Terada, Chem. Pharm. Bull., 17, 2417 (1969); c) M. Koszytkowska-Stawinska, W. Sas, J. Chem. Res. (S), 298 (1998); d) T. Sheradsky, L. Yusupova, Tetrahedron Lett., 36, 7701 (1995); e) S. Toii, H. Okumoto, A. Genba, Chem. Lett., 747 (1996) .
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  • Significant spectral data for 7: 1H NMR (CDCl3) (two amide rotamers in a ratio of 7:3) δ 5.98 (d, J = 6.1 Hz, CH=CH), 5.93 (d, J = 6.1 Hz, CH=CH), 5.45 (d, J = 6.1 Hz, CH=CH), 5.38 (d, J = 6.1 Hz, CH=CH), 4.49 (d, J = 3.5 Hz, CHOMe), 4.47 (d, J = 3.2 Hz, CHOMe), 3.95 (t, J = 9.2 Hz, C-3 glucose), 3.71 (s, CO2Me) and 3.69 (s, CO2Me). LRMS (EI, 70 eV): m/z 673 (M+). Anal. Calcd for C39H47NO9 (673.80): C, 69.52; H, 7.03; N, 2.08. Found: C, 69.30; H, 7.11; N, 2.04.
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  • Anal. Calcd for C39H49NO11 (707.82): C, 66.18; H, 6.98; N, 1.98. Found: C, 65.67; H, 6.80; N, 1.90.
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