3β-O-β-D-glucopyranosyl-14,16β-dihydroxy-5β-card-20(22)-enolide | 32077-87-5

• 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: 3β-O-β-D-glucopyranosyl-14,16β-dihydroxy-5β-card-20(22)-enolide
• 英文别名: 3-O-β-D-glucopyranosyl-Gitoxigenin；3-[(3S,5R,8R,9S,10S,13R,14S,16S,17R)-14,16-dihydroxy-10,13-dimethyl-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
• CAS: 32077-87-5
• 化学式: C₂₉H₄₄O₁₀
• 分子量: 552.662
• InChiKey: IUJWXPVDZQGUQU-VAEILQMJSA-N

物化性质

• 熔点：
  205-212 °C
• 沸点：
  772.6±60.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  39
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  166
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  苯基-BETA-葡萄糖吡喃糖苷 、 芰皂配基 以 水 、 乙腈 为溶剂， 反应 12.0h， 以43.1%的产率得到3β-O-β-D-glucopyranosyl-14,16β-dihydroxy-5β-card-20(22)-enolide
  参考文献：
  名称：

  Enzymic synthesis of chemically unstable cardiac glycosides by β-galactosidase from Aspergillus oryzae

  摘要：

  DOI：

  10.1016/s0040-4039(01)80221-5

文献信息

• Enzymic synthesis of chemically unstable cardiac glycosides by β-galactosidase from Aspergillus oryzae
  作者：Yasuhiro Ooi、Toshihiro Hashimoto、Naoki Mitsuo、Toshio Satoh

  DOI：10.1016/s0040-4039(01)80221-5

  日期：1984.1
• Probing the Regiospecificity of Enzyme-Catalyzed Steroid Glycosylation
  作者：Maoquan Zhou、Yanpeng Hou、Adel Hamza、Chang-Guo Zhan、Tim S. Bugni、Jon S. Thorson

  DOI：10.1021/ol3024924

  日期：2012.11.2

  The potential of a uniquely permissive engineered glycosyltransferase (OleD ASP) as a catalyst for steroid glycosylation is highlighted. The ability of OleD ASP to glucosylate a range of cardenolides and bufadienolides was assessed using a rapid LC-UV/MS-SPE-NMR analytical platform. While a bias toward OleD-catalyzed C3 monoglucosylation was observed, subtle alterations of the steroidal architecture, in some cases, invoked diglucosylation or, in one case (digoxigenin), C12 glucosylation. This latter case represents the first, and highly efficient, synthesis of digoxigenin 12-O-beta-D-glucoside.
• Ooi, Yasuhiro; Hashimoto, Toshihiro; Mitsuo, Naoki, Chemical and pharmaceutical bulletin, 1985, vol. 33, # 4, p. 1808 - 1814
  作者：Ooi, Yasuhiro、Hashimoto, Toshihiro、Mitsuo, Naoki、Satoh, Toshio

  DOI：——

  日期：——