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ChemicalBook CAS DataBase List 3-Isomangostin hydrate
26063-96-7

3-Isomangostin hydrate synthesis

5synthesis methods
-

Yield:26063-96-7 75%

Reaction Conditions:

with toluene-4-sulfonic acid;acetic acid in benzene at 20; for 20 h;

Steps:

3-isomangostin hydrate (4b).

A mixture of 3-isomangostin (13.0 mg, 0.032 mmol) and PTSA (29.6 mg) in acetic acid (0.5 mL) was stirred at room temperature for a 20 h. The reaction mixture was extracted with EtOAc (10 mL 3). The combined organic extract was washed with sat.NaHCO3 and then washed with water BRINE. The resulting mixture was dried over anhydrous Na2SO4 and evaporated at reduced pressure. Chromatography over silica gel with 20% aceteone-hexane as an eluent yielded of 4b (10.3 mg; 75% yield; Rf = 0.31 (20% acetone-hexane)) as a pale lemon-yellow powder (m.p. 182-183 °C). 1H NMR 300 MHz (CDCl3) d (ppm) 13.59 (1H, s, 1-OH), 6.83 (1H, s, H-5), 6.22 (1H, s, H-4), 3.45-3.39 (2H, m, H-1¢¢), 1.85-1.76 (2H, m, H-2¢¢), 1.37 (6H, s, CH3-4¢¢ and CH3-5¢¢), 2.70 (2H, t, J = 6.6 Hz, H-1¢), 1.83 (2H, t, J = 6.6 Hz, H-2¢), 1.33 (6H, s, CH3-4¢ and CH3-5¢), 3.86 (3H, s, 7-OCH3).

References:

Boonnak, Nawong;Chantrapromma, Suchada;Kaewpiboon, Chutima;Sathirakul, Korbtham [Bioorganic and Medicinal Chemistry Letters,2020,vol. 30,# 20,art. no. 127494] Location in patent:supporting information

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