ChemicalBook CAS DataBase List 19-HYDROXYCHOLESTEROL 3-ACETATE

19-HYDROXYCHOLESTEROL 3-ACETATE synthesis

5synthesis methods

Product Name:19-HYDROXYCHOLESTEROL 3-ACETATE
CAS Number:750-59-4
Molecular formula:C29H48O3
Molecular Weight:444.69

5-Bromo-6β,19-epoxy-5α-cholestan-3β-ol acetate

1258-07-7
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750-59-4
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$452.41/5MG

Yield:750-59-4 89%

Reaction Conditions:

with water;acetic acid;zinc at 20; for 75 h;

Steps:

To a stirred solution of bromo ether S3 (1.42 g, 2.71 mmol) in acetic acid and water (15:1, 19.2mL) at rt was added activated zinc dust (3.54 g, 54.2 mmol). After stirring for 21 h, acetic acid (9.00 mL), water (0.60 mL), and activated zinc dust (1.77 g, 27.1 mmol) were supplemented. After 54 h, CH₂Cl₂ (35 mL) was added to the mixture, and insoluble materials were filtered off. The filtrate wasextracted with CH₂Cl₂ (30 mL). The extract was washed with brine (50 mL), dried over Na₂SO₄, and concentrated in vacuo. The residue (1.19 g) was purified by silica gel column chromatography (25 g,EtOAc/hexane = 2:8) to give homoallylic alcohol S4 (1.08 g, 89%) as a white solid: Rf 0.38 (Et₂O/hexane = 1:1); ¹H NMR (400 MHz, CDCl₃) δ 5.74 (d, J = 5.2 Hz, 1H), 4.61 (m, 1H), 3.80 (d, J= 11.2 Hz, 1H), 3.59 (d, J = 11.2 Hz, 1H), 2.39 (m, 1H), 2.23 (m, 1H), 2.03-1.90 (m, 6H), 1.85-1.74 (m, 3H), 1.61-1.45 (m, 6H), 1.33-1.21 (m, 4H), 1.19-0.99 (m, 9H), 0.92-0.87 (m, 5H), 0.83 (dd, J =6.6, 2.0 Hz, 6H), 0.70 (s, 3H). Other data were identical to those reported.²

References:

Oikawa, Yuya;Uchiyama, Daiki;Shirasawa, Takuya;Oikawa, Masato;Ishikawa, Yuichi [Tetrahedron Letters,2016,vol. 57,# 35,p. 3949 - 3951] Location in patent:supporting information