![](/CAS/20180808/GIF/25166-14-7.gif)
2,3-Dehydrosilybin A synthesis
- Product Name:2,3-Dehydrosilybin A
- CAS Number:25166-14-7
- Molecular formula:C25H20O10
- Molecular Weight:480.42
![Silybin](/CAS/GIF/22888-70-6.gif)
22888-70-6
461 suppliers
$5.00/25mg
![2,3-Dehydrosilybin A](/CAS/20180808/GIF/25166-14-7.gif)
25166-14-7
9 suppliers
inquiry
Yield:25166-14-7 91%
Reaction Conditions:
with pyridine;iodine;magnesium chloride at 100; for 1 h;Temperature;Reagent/catalyst;Time;
Steps:
2.1 Typical experimental procedure for the synthesis of 2,3-dehydrosilybin (DHS)
A solution of Silybin (100 mg, 0.2 mmol) and iodine (50 mg, 0.2 mmol) in pyridine (4.0 mL) was added anhydrous metal chloride (0.4 mmol), and the reaction mixture was stirred at 100 °C for 1 h, then the solvent was removed under reduced pressure. Sodium dithionite (150 mg), distilled water (25.0 mL) and H3PO4 (85%, 2.0 mL) were added to the mixture and stirred at room temperature for 3 h, then filtered and washed with water. The filter residue was extracted with EtOAc (3 × 50 mL), then dried with anhydrous Na2SO4. The solvent was evaporated under reduced pressure and the residue was purified by silica gel flash chromatography using petroleum ether/actone (3/2, v/v) as eluent to give pure product DHS. 1H NMR (400 MHz, DMSO-d6) δ 12.43 (s, 1H, 5-OH), 10.87 (s, 1H, 7-OH), 9.62 (s, 1H, 3-OH), 9.21 (s, 1H, 20-OH), 7.88-7.69 (m, 2H, 13-H and15-H), 7.14 (d, J = 8.7 Hz, 1H, 16-H), 7.05 (d, J = 1.8 Hz, 1H, 18-H), 6.90 (dd, J = 8.1, 1.8 Hz, 1H, 22-H), 6.82 (d, J = 8.1 Hz, 1H, 21-H), 6.47 (d, J = 2.0 Hz, 1H, H-8), 6.20 (d, J = 2.0 Hz, 1H, H-6), 5.03 (t, J = 5.3 Hz, 1H, 23-OH), 4.97 (d, J = 8.0 Hz, 1H, 11-H), 4.37-4.19 (m, 1H, 10-H), 3.80 (s, 3H, 19-OCH3), 3.57 (d, J = 13.1 Hz, 1H, 23-H); 13C NMR (100 MHz, DMSO-d6) δ 176.47, 164.58, 161.16, 156.70, 148.12, 147.54, 146.20, 145.50, 143.85, 136.80, 127.69, 124.22, 121.74, 121.05, 117.33, 116.68, 115.79, 112.16, 103.55, 98.75, 94.06, 78.98, 76.36, 60.56, 56.17. HRESIMS m/z 481.11414 [M+H]+ (calcd for C25H21O10, 481.11347); 503.09655, [M+Na]+ (calcd for C25H20NaO10, 503.09542). Consistent with the reported literatures.
References:
Wen, Yong-ju;Zhou, Zong-yuan;Zhang, Guo-lin;Lu, Xiao-xia [Tetrahedron Letters,2018,vol. 59,# 17,p. 1666 - 1669] Location in patent:supporting information
![Silybin](/CAS/GIF/802918-57-6.gif)
802918-57-6
36 suppliers
$8.00/1000mg
![2,3-Dehydrosilybin A](/CAS/20180808/GIF/25166-14-7.gif)
25166-14-7
9 suppliers
inquiry