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    ChemicalBook CAS DataBase List Chenodeoxycholic acid
    474-25-9

    Chenodeoxycholic acid synthesis

    8synthesis methods
    -

    Yield:474-25-9 97%

    Reaction Conditions:

    with water;sodium hydroxide in methanol; for 1 h;Reflux;

    Steps:

    2.2.9. 2β, 3, 6α-Trihydroxyl-5β-cholanoate (H9/H10)

    General procedure: To a stirred solution of compound H8 (3α)(0.1011g, 0.2mmol) in MeOH (4mL) and H2O (1mL) was added NaOH (0.0441g, 1.1mmol) at room temperature. The mixture was heated at reflux for 1h, and then adjusted to pH 1-2 with 1M HCl aq to afford compound 2β, 3α, 6α-trihydroxyl-5β-cholanoate H9 (0.0794g, 90% yield) as white solid; mp 52-55°C; (α)20D αD20 =-9.2 (c=0.5, CH2Cl2); FTIR (KBr, cm-1) 3443 (O-H), 1704 (C=O), 1025 and 1023 (C-O); HRMS (ESI, m/z) Calcd for C24H40O5 408.2876; found: 431.2751 [M+Na]+ (Calcd 431.2773). H9 1H NMR (600MHz, CD3OD) δ 4.08 (dt, J=11.1, 4.2Hz, 1H, 6β-H), 4.02-3.96 (m, 1H, 2α-H), 3.68-3.61 (m, 1H, 3β-H), 1.00 (s, 3H, 19-H), 0.98 (d, J=6.5Hz, 3H, 21-H), 0.72 (s, 3H, 18-H); 13C NMR (151MHz, CD3OD) δ 176.7 (C-24), 68.9 (C-3), 67.1 (C-6), 67.0 (C-2), 56.1, 55.9, 42.6, 42.1, 40.4, 39.9, 37.8, 37.7, 35.3, 34.8, 33.9, 30.9, 30.6, 27.8, 25.5, 23.8, 22.9, 20.9, 17.4, 11.0.

    References:

    Liang, Yu-Yan;Huang, Huan;Li, Yang;Du, Rong-Kai;Li, Jing;Liu, Yong-Hong;Li, Shan;Zhang, Lei [Steroids,2020,vol. 157,art. no. 108594]

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