Synthesis of Functionalized Thiodisaccharides by Conjugate Addition

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• Typical procedure: The saccharide acceptor (0.5 mmol) and the thioglucose (1, 200 mg, 0.57 mmol) were stirred in chloroform (10 mL) at room temperature and triethylamine (2 μL) was added. Stirring was continued for 30 min, the solvent evaporated and the raw material purified by crystallisation or chromatography.
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• Representative physical data: (3) mp 161–164 °C, [α]D 20 −125° (c 1, chloroform), 1H NMR (400 MHz, CDCl3): δ 5.14 (s, 1 H, H-1), 4.59 (d, 1 H, J1′,2′ = 10.2 Hz, H-1′), 3.98–4.06 (m, 2 H, H-6endo and H-6exo), 3.58 (m, 1 H, H-4), 3.09 (dd, 1 H, J3eq.4 = 8.1 Hz, Jgem = 17.8 Hz, H-3eq), 2.04 (dd, 1 H, J3ax,4 = 1.5 Hz, H-3ax). (5) mp 56 °C, [α]D 20 +43° (c 1, chloroform), 1H NMR (400 MHz, CDCl3). δ 4.99 (d, 1 H, J1,2 = 4.4 Hz, H-1), 4.65 (d, 1 H, J1′.2′ = 10.1 Hz, H-1′), 4.11 (dd, J5.6a = 1.9 Hz, H-5), 3.43 (s, 3 H, OMe), 3.41 (dd, 1-H, Jgem = 9.2 Hz, H-6a), 3.32 (dd, 1 H, H-6b), 3.25 (dt, 1 H, J2.3ax = 8.2 Hz, H-2), 2.61 (m, 2 H, H-3ax and H-3eq); (7) 1H NMR (400 MHz, CDCl3): δ = 5.16 (dd, 1 H, J1,2ax = 12.2 Hz, J1.2eq = 3.1 Hz, H-1), 4.65 (d, 1 H, J1,2 = 9.6 Hz, H-1′), 4.38 (d, 1 H, J4.5 = 10.2 Hz, H-4), 4.06 (dd, 1 H, J5.6a = 5.6 Hz, Jgem = 10.2 Hz, H-6a), 3.94 (dd, 1 H, J5.6b = 10.2 Hz, H-6b), 3.59 (ddd, 1 H, H-5), 2.80 (dd, 1 H, Jgem = 14.8 Hz, H-2ax), 2.71 (dd, 1 H, H-2eq), 1.52 (s, 3 H, CH3), 1.50 (s, 3H, CH3).
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