ouabain 1,2',3',4',11,19-hexaacetate | 57198-85-3

• 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: ouabain 1,2',3',4',11,19-hexaacetate
• 英文别名: ouabain hexaacetate；(2R,3R,4R,5S,6S)-2-(((1R,3S,5S,10R,11R,13R,14S,17R)-1,11-diacetoxy-10-(acetoxymethyl)-5,14-dihydroxy-13-methyl-17-(5-oxo-2,5-dihydrofuran-3-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl)oxy)-6-methyltetrahydro-2H-pyran-3,4,5-triyl triacetate；1β,11α,19-triacetoxy-5,14-dihydroxy-3β-(tri-O-acetyl-α-l-rhamnopyranosyloxy)-5β,14β-card-20(22)-enolide；1β,11α,19-Triacetoxy-5,14-dihydroxy-3β-(tri-O-acetyl-α-l-rhamnopyranosyloxy)-5β,14β-card-20(22)-enolid；[(1R,3S,5S,8R,9S,10R,11R,13R,14S,17R)-1,11-diacetyloxy-5,14-dihydroxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-3-[(2R,3R,4R,5S,6S)-3,4,5-triacetyloxy-6-methyloxan-2-yl]oxy-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-10-yl]methyl acetate
• CAS: 57198-85-3
• 化学式: C₄₁H₅₆O₁₈
• 分子量: 836.885
• InChiKey: HHKMFKOZFVNPCO-QLBXPCGRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  59
• 可旋转键数：
  16
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  243
• 氢给体数：
  2
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  ouabain 1,2',3',4',11,19-hexaacetate 在 sodium hydroxide 、 sodium periodate 、 potassium hydrogencarbonate 、 臭氧 、 溶剂黄146 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 为溶剂， 反应 12.0h， 生成 3β-(α-L-rhamnopyranosyl)oxy-21-nor-5β-pregnane-1β,5,11α,14β,19,20-hexol
  参考文献：
  名称：

  Pregnane and 21-norpregnane derivatives of ouabain that bind to the digitalis receptor

  摘要：

  14 beta-Hydroxy-5 beta-pregnane and 14 beta-hydroxy-21-nor-5 beta-pregnane derivatives of ouabain were synthesised and their structures established by NMR measurements. Binding affinity in an [H-3]ouabain radioligand binding assay was determined. Pregnane derivatives of ouabain are more polar than pregnane rhamnoside derivatives of digitoxigenin. Whereas ouabain binds similarly to digitoxigenin rhamnoside, the pregnane derivatives of ouabain have significantly weaker binding affinity than their congeners from digitoxigenin.

  DOI：

  10.1016/0223-5234(94)90140-6
• 作为产物：
  描述：

  G毒毛旋花苷 、 乙酸酐 以88%的产率得到ouabain 1,2',3',4',11,19-hexaacetate
  参考文献：
  名称：

  Strophanthus Tholloni Franch种子的糖苷。第二次沟通。糖苷和糖苷配基，第179部分

  摘要：

  从Strophanthus Tholloni Franch的种子中提取。发酵后为9晶体。游离形式的糖苷和其结晶形式的另外6种糖苷。分离出乙酰基衍生物。第16种物质（名词γ）只能分离为无定形但实际上是均匀的形式。另外，通过纸色谱法检测到少量的其他两种糖苷（R，S）。

  DOI：

  10.1002/hlca.19570400413

文献信息

• CONTRACEPTIVE AGENTS
  申请人：Blanco Gustavo

  公开号：US20140005132A1

  公开（公告）日：2014-01-02

  The invention provides compounds of formula I, II, III, or IV: wherein R 1 to R 11 , X, and Y have any of the values defined in the specification. The compounds inhibit Na, K-ATPase α4 and are useful as contraceptive agents.

  这项发明提供了式I、II、III或IV的化合物： 其中R1至R11、X和Y具有规范中定义的任何值。这些化合物抑制Na、K-ATPase α4，并可用作避孕剂。
• Novel annulation products derived by selective attack on the C(18) angular methyl group of the cardenolide ouabain
  作者：E.J Corey、Brian M Stoltz

  DOI：10.1016/s0040-4039(99)00165-3

  日期：1999.3

  Selective reactions at the C(18) angular methyl group of ouabain derivatives employing rhodium- and photochemically-mediated CC bond formation allow the synthesis of annulation products 4 and 13.

  使用铑和光化学介导的CC键形成的哇巴因衍生物的C（18）角甲基的选择性反应可合成环状产物4和13。
• Weitere Abbauversuche mit Ouabagenin (II). Glykoside und Aglykone, 41. Mitteilung
  作者：R. F. Raffauf、T. Reichstein

  DOI：10.1002/hlca.19480310729

  日期：——

  AbstractDie Bildung von 2 verschiedenen Tetraacetaten A und B aus analysen‐reinem Ouabagenin wird bestätigt. Vorsichtige saure Hydrolyse von Monoaceton‐ouabagenin‐diacetat sowie von Anhydro‐ouaba‐genin‐diacetat gibt 2 verschiedene Stoffe, wahrscheinlich Di‐acetate, die als α‐ und β‐Ouabagenin‐diacetat bezeichnet werden. Jedes gibt bei weiterer Acetylierung wieder die Tetraacetate A und B.
• Mannich; Siewert, Chemische Berichte, 1942, vol. 75, p. 737,743
  作者：Mannich、Siewert

  DOI：——

  日期：——
• Microgram-Scale Testing of Reaction Conditions in Solution Using Nanoliter Plugs in Microfluidics with Detection by MALDI-MS
  作者：Takuji Hatakeyama、Delai L. Chen、Rustem F. Ismagilov

  DOI：10.1021/ja057720w

  日期：2006.3.1

  This paper describes a microfluidic system to screen and optimize organic reaction conditions on a submicrogram scale. The system uses discrete droplets (plugs) as microreactors separated and transported by a continuous phase of a fluorinated carrier fluid. Previously, we demonstrated the use of a microfabricated PDMS plug-based microfluidic system to perform assays and crystallization experiments in aqueous solutions with optical detection. Here, we developed an approach that does not require microfabrication of microfluidic devices, is applicable to synthetic reactions in organic solvents, and uses detection by MALDI-MS. As a demonstration, conditions for selective deacetylation of ouabain hexaacetate were tested, and the optimum conditions for mono-, bis-, or trisdeacetylation have been identified. These conditions were validated by scale-up reactions and isolating these potentially neurotoxic products. Mono- and bisdeacetylated products are unstable intermediates in the deacetylation and were isolated for the first time. This system enables no-loss handling of submicroliter volumes containing a few micrograms of a compound of interest. It could become valuable for investigating or optimizing reactions of precious substrates (e.g., products of long synthetic sequences and natural products that can be isolated only in small quantities).