ChemicalBook CAS DataBase List 1-Isomangostin

1-Isomangostin synthesis

5synthesis methods

Product Name:1-Isomangostin
CAS Number:19275-44-6
Molecular formula:C24H26O6
Molecular Weight:410.46

6147-11-1 Synthesis

6147-11-1
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19275-46-8
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19275-44-6
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Yield:19275-46-8 65% ，19275-44-6 15%

Reaction Conditions:

with toluene-4-sulfonic acid in benzene; for 0.5 h;Reflux;Dean-Stark;

Steps:

3-isomangostin (4a)^5C and 1-isomangostin.

A mixture of a-mangostin (150.0 mg, 0.37 mmol) and PTSA (172.0 mg) in dry benzene (11 mL) was refluxed over a water bath with a Dean-Stark apparatus for a 30 mins. Benzene was removed, and the residue was extracted with CHCl₃ (3 x 50 mL). The organic layer was washed with H₂O (2 x 50 mL) and dried with anhydrous over anhydrous MgSO₄. Chromatography over silica gel with 15% aceteone-hexane as an eluent yielded of 4a (98.7 mg, 65% yield; R_f = 0.53 (20% acetone-hexane)) and 4a-1 (22.7 mg, 15% yield; R_f = 0.71 (20% acetone-hexane)). 3-isomangostin (4a) Yellow powder (m.p. 164-166 °C). ¹H NMR 300 MHz (CDCl₃) d (ppm) 13.72 (1H, s, 1-OH), 6.82 (1H, s, H-5), 6.22 (1H, s, H-4), 5.27 (1H, br t, J = 6.6 Hz, H-2￠￠), 4.09 (2H, d, J = 6.6 Hz, H-1￠￠), 1.85 (3H, s, CH₃-5￠￠), 1.69 (3H, s, CH₃-4￠￠), 2.71 (2H, t, J = 6.9 Hz, H-1￠), 1.85-1.81 (2H, m, H-2￠), 1.37 (6H, s, CH₃-4￠ and CH₃-5￠), 3.80 (3H, s, 7-OCH₃). 1-isomangostin (4a-1). Yellow powder (m.p. 164-166 °C). ¹H NMR 300 MHz (CDCl₃) d (ppm) 6.82 (1H, s, H-5), 6.22 (1H, s, H-4), 5.27 (1H, br t, J = 6.6 Hz, H-2￠￠), 4.09 (2H, d, J = 6.6 Hz, H-1￠￠), 1.85 (3H, s, CH₃-5￠￠), 1.69 (3H, s, CH₃-4￠￠), 2.67 (2H, t, J = 6.9 Hz, H-1￠), 1.85-1.81 (2H, m, H-2￠), 1.42 (6H, s, CH₃-4￠ and CH₃-5￠), 3.80 (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

6147-11-1
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$39.00/10mg