3.12.6. Methyl 3-Deoxy-3-*C*-(3-Fluorophenylureido)Methyl-β-d-Galactopyranoside **5**

Compound **5** (TLC, DCM/MeOH, 10:1, R<sup>f</sup> 0.44) was prepared according to the general procedure *3.12* from **20** (50 mg, 0.0814 mmol). Obtained as a colorless oil in 41% yield (11.5 mg, 0.03 mmol) from flash column chromatography (DCM:MeOH 12:1–5:1). [α] 25 <sup>D</sup> <sup>−</sup>17.3 (c 0.6, CH3OH). <sup>1</sup>H NMR (CD3OD, 400 MHz): 7.34 (dt, 1H, *J* 12.0 Hz, *J* 2.0 Hz, Ar*H*), 7.24–6.64 (m, 3H, Ar*H*), 4.44 (d, 1H, *J* 7.2 Hz, H-1), 3.90–3.83 (m, 3H, H-2, H-4, H-5), 4.22 (t, 1H, *J* 8.8 Hz, C*H*2OH), 4.08 (bs, 1H, H-4), 3.97–3.94 (m, 2H, H-2, H-5), 3.78–3.76 (d, 2H, H-6a, H-6b), 3.52 (s, 3H, OC*H*3), 3.47 (dd, 1H, *J* 14.4 Hz, *J* 6.4 Hz, C*H*2NHCONH), 3.41 (dd, 1H, *J* 14.4 Hz, *J* 7.6 Hz, C*H*2NHCONH), 2.27–2.21 (m, 1H, H-3). <sup>13</sup>C NMR (CD3OD, 100 MHz): 164.5 (d, *J* 240 Hz), 158.0, 143.0 (d, *J* 11 Hz), 131.0 (d, *J* 9.8 Hz), 115.2 (d, *J* 3.2 Hz), 109.4 (d, *J* 22 Hz), 106.7 (d, *J* 22 Hz), 103.8, 76.1, 69.2, 69.0, 63.0, 56.9, 46.8, 38.0. HRMS calcd for C15H21FN2O6+H<sup>+</sup> (M+H)+: 354.1462, found: 345.1459.
