Thesis-Final 03 June 2011 pdf - Jacobs University

Annex Chapter 6
36.47 (C-2), 36.93 (C-6), 63.46 (C-4), 63.81 (C-3), 75.75 (C-5), 77.47 (C-1), 109.65
(C-12), 109.82 (C-21), 110.01 (C-30), 115.74 (C-9), 116.34 (C-18), 116.52 (C-27),
119.23 (C-15), 119.34 (C-24), 119.81 (C-33), 122.84 (C-16), 124.65 (C-25), 125.24
(C-34), 132.63 (C-11), 133.46 (C-20), 133.93 (C-29), 144.64 (C-10), 145.15 (C-19),
145.82 (C-28), 146.23 (C-13), 146.45 (C-22), 146.93 (C-31), 148.63 (C-14) 149.26
(C-23), 149.54 (C-32), 162.22 (C-8), 162.51 (C-17), 162.65 (C-26), 167.92 (C-35),
168.16 (C-37), 168.34 (C- 39), 168.77 (C-36), 168.98 (C-38), 169.14 (C-40), 173.26
(C-7); MS, m/z (ESI): 935.2005 [M + - C 46 H 40 O 20 and C 46 H 40 O 20 Na requires
935.2005]
(1R, 3R, 4S, 5R)-1-(β, β, β-trichloroethoxycarbonyl)-3,4,5-tri-
(acetylferuloyl) quinic acid, (109)-154
To a solution of Troc-quinide (0.300 g, 0.858 mmol) and DMAP (0.052 g, 0.429
mmol) in dichloromethane (5 ml) were added acetyl ferulic acid chloride (0.436 g,
1.716 mmol) in triethylamine (0.5 ml). The reaction solution was stirred for 16 hours
at room temperature. The reaction solution was extracted with dichloromethane (50
ml) and 2M HCl (10 ml). The organic phase was dried with MgSO4, filtered and the
solvent was removed under reduced pressure. The purification of compound carried
out by flash chromatography on silica gel eluting with chloroform-acetone (8:2) to
afford (1R, 3R, 4S, 5R)-1-(β, β, β-trichloroethoxycarbonyl)-3,4,5-tri-
250