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1H NMR (Bruker Avance 400, 400 MHz, CDCl3) for compound 4: δ = 6.56 (d, 1 H, J = 10.1 Hz, H-1), 5.55 (t, 1 H, J = 9.7 Hz, H-3), 5.21 (t, 1 H, J = 9.7 Hz, H-4), 4.44 (t, 1 H, H-2), 4.28 (dd, 1 H, J = 12.5 Hz, J = 4.7 Hz, H-6), 4.15 (dd, 1 H, J = 2.3 Hz, H-6′), 3.85 (ddd, 1 H, H-5), 2.14 (s, 3 H, Ac), 2.08 (s, 3 H, Ac), 2.02 (s, 3 H, Ac), 1.99 (s, 3 H, DMM), 1.91 (s, 3 H, DMM).
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21 To a solution of compound 1 and 2 (0.66 mmol, 1 equiv) in CH2Cl2 (3 mL) at 0 °C TMSI (1.1 equiv) was added under inert atmosphere. The reaction mixture was stirred at r.t. until disappearance of the starting material (about 30 min), then cooled to -78 °C. On the other hand, compound 3 (0.63 mmol, 1 equiv) was dissolved in toluene (3 mL) and TMSI (1.1 equiv) was added at 0 °C under inert atmosphere. The solution was stirred at 80 °C for 45 min, then the solvent was evaporated. The residue was dissolved in CH2Cl2 (3 mL) under inert atmosphere and the solution cooled at -78 °C. The nucleophile and the acidic promoter (when necessary, see text) were added, the solution was allowed to reach r.t. and stirred for 6-8 h. Standard workup and silica gel chromatography gave the β-glycoside. When silylated compound 2 was employed as starting material (entries 10-13 in Table
[1]
), MeOH was added after glycosylation to remove the trimethylsilyl groups. After stirring 20 min, the solvent was evaporated in vacuo and the crude residue was submitted to standard acetylation.
22
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