18,20-epoxy-condurangogenin C | 81426-56-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 18,20-epoxy-condurangogenin C
• CAS: 81426-56-4
• 化学式: C₃₄H₄₄O₈
• 分子量: 580.719
• InChiKey: OERKULKHKXNDMT-HKXQWGTOSA-N

反应信息

• 作为反应物：
  描述：

  18,20-epoxy-condurangogenin C 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以16.0 mg的产率得到18,20-epoxy-deacyl condurangogenin C
  参考文献：
  名称：

  Studies on the constituents of asclepiadaceae plants. LI. Oxidation at the 18-methyl group of C/D-cis-pregnane type steroids and 13C-nuclear magnetic resonance spectra of 18-oxygenated pregnanes and related compounds.

  摘要：

  合成了四种18-氧化孕烷类甾体；18, 20-环氧孕-5-烯-3β-醇乙酸酯（III）、18, 20-环氧异喹啉环状亚硫酸酯（VIII）、18, 20-环氧去酰基康杜兰根烯C（XVIII）和18, 20-环氧-20-环氧去酰基康杜兰根烯C（XXI），并通过化学和光谱研究确定了它们的结构。发现20R和20S-羟基C/D-顺式孕烷类甾体之间的13C核磁共振化学位移有显著差异。

  DOI：

  10.1248/cpb.30.3932
• 作为产物：
  描述：

  condurangogenin C 3-acetate 在 lead(IV) acetate 、 sodium tetrahydroborate 、 碘 、 calcium carbonate 作用下， 以 环己烷 为溶剂， 反应 25.0h， 生成 18,20-epoxy-condurangogenin C
  参考文献：
  名称：

  Studies on the constituents of asclepiadaceae plants. LI. Oxidation at the 18-methyl group of C/D-cis-pregnane type steroids and 13C-nuclear magnetic resonance spectra of 18-oxygenated pregnanes and related compounds.

  摘要：

  合成了四种18-氧化孕烷类甾体；18, 20-环氧孕-5-烯-3β-醇乙酸酯（III）、18, 20-环氧异喹啉环状亚硫酸酯（VIII）、18, 20-环氧去酰基康杜兰根烯C（XVIII）和18, 20-环氧-20-环氧去酰基康杜兰根烯C（XXI），并通过化学和光谱研究确定了它们的结构。发现20R和20S-羟基C/D-顺式孕烷类甾体之间的13C核磁共振化学位移有显著差异。

  DOI：

  10.1248/cpb.30.3932

文献信息

• Studies on the constituents of asclepiadaceae plants. XLIX. Confirmation of the structures of antitumor-active glycosides in condurango cortex. Chemical transformation of the aglycone moiety.
  作者：MUNEAKI TAKASE、SUMIO TERADA、HAJIME YAMAMOTO、TOSHIHARU NARITA、MASAHIKO KIMURA、KOJI HAYASHI、HIROSHI MITSUHASHI

  DOI：10.1248/cpb.30.2429

  日期：——

  In order to confirm the structure of condurangogenin B, which is the aglycone of antitumor-active condurango glycoside (CG) B0, the hypoiodite reaction of condurangogenin C 3-acetate, was carried out. A mixture of condurangogenin C 3-acetate, Pb (OAc)4, I2, CaCO3, and diethyl ether was irradiated under nitrogen using a tungsten lamp. HPLC separation of the reaction products gave three compounds, P-1, P-2, and P-3. The structures of these compounds were determined from the spectroscopic data. The PMR and mass spectra of P-1 were essentially identical with those of condurangogenin B 3-acetate. Thus, the ester linkage positions (11-cinnamoyl, 12-acetyl) and the ketal structure of conduragogenin B were confirmed. As CGD0, 20-O-methyl-CGD0, and 20-iso-O-methyl-CGD0 could be converted chemically to CGB0, these glycosides have the same positions of ester linkages as CGB0.