3.12.4. Methyl 3-Deoxy-3-*C*-Methoxymethyl-β-d-Galactopyranoside **3**

Compound **3** (TLC, DCM/MeOH, 10:1, R<sup>f</sup> 0.5) was prepared according to the general procedure *3.12* from **16** (36 mg, 0.07 mmol). Obtained as a colorless oil in 64% yield (10.4 mg, 0.05 mmol). [α] 25 D <sup>−</sup>33.4 (c 0.5, CH3OH) from flash column chromatography (DCM:MeOH 15:1–9:1). <sup>1</sup>H NMR (CD3OD, 400 MHz): 4.41 (d, 1H, *J* 7.6 Hz, H-1), 3.93 (dd, 1H, *J*4,5 3.2 Hz, *J*3,4 2.0 Hz, H-4), 3.88–3.82 (m, 2H, H-2, H-5), 3.73 (d, 2H, *J* 6.0 Hz, H-6a, H-6b), 3.65 (dd, 1H, *J* 10.0 Hz, *J* 4.8 Hz, CH2OCH3), 3.57 (dd, 1H, *J* 10.0 Hz, *J* 4.8 Hz, CH2OCH3), 3.50 (s, 3H, OC*H*3), 3.33 (s, 3H, OC*H*3), 2.38–2.34 (m, 1H, H-3). <sup>13</sup>C NMR (CD3OD, 100 MHz): 104.1, 76.3, 70.2, 68.7, 68.5, 63.1, 59.1, 56.8, 46.6. HRMS calcd for C9H18O6+Na<sup>+</sup> (M+Na)+: 245.1001, found: 245.1004.

3.12.5. Methyl 3-Deoxy-3-*C*-[4-(3-Fluorophenyl)-1H-1,2,3-Triazol-1-Ylmethyl]-β-d-Galactopyranoside **4**

Compound **4** (TLC, DCM/MeOH, 10:1, R<sup>f</sup> 0.43) was prepared according to the general procedure *3.12* from triazole **18** (55 mg, 0.09 mmol). Obtained as a colorless oil in 78% yield (24.3 mg, 0.07 mmol) from flash column chromatography (DCM:MeOH 20:1–9:1). [α] 25 <sup>D</sup> <sup>−</sup>20.5 (c 0.7, CH3OH). <sup>1</sup>H NMR (CD3OD, 400 MHz): 8.40 (s, 1H, Ar*H*), 7.65–7.05 (m, 4H, Ar*H*), 4.80 (dd, 1H, *J* 14.4 Hz, *J* 6.0 Hz, C*H*2N3C8H5F), 4.63 (dd, 1H, *J* 14.4 Hz, *J* 9.2 Hz, C*H*2OH), 4.48 (d, 1H, *J* 6.4 Hz, H-1), 4.02–3.99 (m, 1H, H-5), 3.82–3.78 (m, 4H, H-2, H-4, H-6a, H-6b), 3.53 (s, 3H, OC*H*3), 2.72–2.66 (m, 1H, H-3). <sup>13</sup>C NMR (CD3OD, 100 MHz): 164.3 (d, *J* 243 Hz), 147.7 (d, *J* 3.1 Hz), 134.0 (d, *J* 8.3 Hz), 131.8 (d, *J* 8.4 Hz), 123.4, 122.4 (d, *J* 2.5 Hz), 115.9 (d, *J* 21 Hz), 113.2 (d, *J* 23 Hz), 103.6, 75.8, 68.0, 67.4, 62.8, 56.8, 48.2, 46.8. HRMS calcd for C16H20FN3O5+H<sup>+</sup> (M+H)+: 354.1465, found: 354.1462.
