HCID 11354944, compound → Kaempferol 3-O-(3′′,4′′-di-O-acetyl-α-L-rhamnopyranoside)

Participants

Reaction Steps

A suspension containing 0.26 g (0.29 mmol) of 10 and 0.10 g of Pd(OH)2/C in 10 mL of 1:1 THF-MeOH was purged with H2 and maintained under a H2 atmosphere for 1 h. The reaction mixture was then diluted with ethyl acetate, filtered through a Celite pad and washed with ethyl acetate. The filtrate was concentrated under diminished pressure to give 1 as a tan solid: yield 0.14 g (94%); silica gel TLC Rf 0.35 (1:1:0.1 hexanes-ethyl acetate-methanol); [α]D17−106.5 (c 0.65, MeOH); 1H NMR (acetone-d6) δ 0.86 (d, 3H, J=6.3 Hz), 1.32 (br s, 1H), 2.01 (s, 3H), 2.06 (s, 3H), 3.54 (m, 1H), 4.48 (d, 1H, J=2.1 Hz), 5.12 (m, 1H), 5.23 (dd, 1H, J=9.9, 2.7 Hz), 5.61 (d, 1H, J=0.9 Hz), 6.32 (brs, 1H), 6.53 (brs, 1H), 7.09 (d, 2H, J=8.4 Hz), 7.90 (d, 2H, J=8.1 Hz), 9.44 (br s, 2H) and 12.62 (br s, 1H); 13C NMR (acetone-d6) δ 17.0, 20.2, 68.7, 70.5, 71.7, 94.1, 99.2, 101.5, 105.2, 115.9, 121.8, 131.1, 134.8, 157.5, 158.0, 160.5, 162.7, 164.6, 169.7, 170.1 and 178.5; mass spectrum (FAB), m/z 517.1345 (M+H)+ (C25H25O12 requires 517.1346).

Provenance & Evidence