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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 26, 1996 - Issue 11
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Original Articles

Highly Stereoselective Synthesis of a C2-Symmetric 2,2′-Bipyridine Derived from Glucose

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Pages 2223-2228 | Received 15 Dec 1995, Published online: 21 Aug 2006

References and Notes

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  • Crystal data for C17H22BrNO6: Monoclinic crystal system, space group P21, a = 5.5543 (8), b = 18.656 (3), c = 9.1122 (15) Å, β = 104.113 (13)°, V = 918.2 (5) Å3, Z = 2, Dc = 1.506 Mg/m3, MoKα radiation, λ = 0.71073 Å, Siemens R3m/V Diffractometer. Out of 5598 reflections (4.0 ° < 2Θ < 45 °), 2181 unique reflections [F˚ > 4.0 σ (F˚)] were used in the refinement (227 parameters), converging to R = 0.0542 and Rw = 0.0565. Absolute configuration of the molecule was confirmed. The sugar has a pseudorotation angle of 61.5 ° with a 4T0 conformation. Atomic coordinates, bond lengths and angles and thermal parameters have been deposited at the Cambridge Crystallographic Data Centre.
  • Tiecco , M. , Testaferri , L. , Tingoli , M. , Chianelli , D. and Montanucci , M. 1984 . Synthesis , : 736 This method was essentially the method reported earlier:, Compound 7 gave 1H and 13C NMR spectra consistent with the assigned structure and a satisfactory elemental analysis was obtained: 1H NMR (CDCl3, 500 MHz): δ 8.22 (d, 1 H, J = 7.8 Hz), 7.88 (t, 1 H, J = 7.8 Hz), 7.74 (d, 1 H, J = 7.8 Hz), 6.30 (d, 1 H, J = 3.4 Hz), 4.75 (d, 1 H, J = 3.9 Hz), 4.25 (d, 1 H, J = 6.4 Hz), 3.67 - 3.62 (m, 2 H), 3.54 (s, 1 H), 3.38 - 3.33 (m, 1 H), 1.70 (s, 3 H), 1.46 (s, 3 H), 1.42 (s, 3 H), 1.20 (s, 3 H); 13C NMR (CDCl3): δ 158.35, 154.22, 137.51, 121.74, 120.06, 112.93, 109.00, 106.07, 84.15, 83.85, 82.12, 73.87, 66.10, 27.15, 26.79, 26.64, 25.26. Anal. Calcd. for C34H44N2O12: C, 60.70; H, 6.59; N, 4.16. Found: C, 60.55; H, 6.47; N, 4.05.

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