ChemicalBook CAS DataBase List 3-Isomangostin hydrate

3-Isomangostin hydrate synthesis

5synthesis methods

Product Name:3-Isomangostin hydrate
CAS Number:26063-96-7
Molecular formula:C24H28O7
Molecular Weight:428.47

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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; R_f = 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

6147-11-1 Synthesis