Reagents and conditions: (a) 10% Pd/C cartridge (s-cart, 30 × 4 mm i.d.), 1
bar (full H2 mode), 25 °C, 1 mL min–1; (b)
LiAlH4, THF, 0 °C → rt; (c) SnCl2, HCl 12 M,
Et2O, (CH2O)n, 70 °C; (d)
CH2N2, Et2O, 0 °C → rt; (e)
methyl-1-bromo-2,3,4-tri-O-acetyl-α-d-glucuronate
(13), Fetizon reagent, molecular sieves, toluene; (f)
Na2CO3, MeOH, rt.