gomophoside | 36597-51-0

• 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: gomophoside
• 英文别名: gomphoside；3-[(1S,3R,5S,7R,9R,10S,12R,14S,15S,18R,19R,22S,23R)-9,10,22-trihydroxy-7,14,18-trimethyl-4,6,11-trioxahexacyclo[12.11.0.03,12.05,10.015,23.018,22]pentacosan-19-yl]-2H-furan-5-one
• CAS: 36597-51-0
• 化学式: C₂₉H₄₂O₈
• 分子量: 518.648
• InChiKey: OFKILMDHPMNNBF-XJSPWRDXSA-N

物化性质

• 熔点：
  234-242 °C(Solv: methanol (67-56-1); water (7732-18-5))
• 沸点：
  699.8±55.0 °C(Predicted)
• 密度：
  1.320±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  37
• 可旋转键数：
  1
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  115
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  gomophoside 在 盐酸 、 双氧水 作用下， 以 甲醇 为溶剂， 反应 192.0h， 以82%的产率得到gomophogenin
  参考文献：
  名称：

  Synthesis of acetates of gomphogenin and gomphoside and evaluation of structure-activity relationships

  摘要：

  Acetates of gomphogenin and gomphoside have been synthesized and their structures established by NMR measurements, optical rotation, mass and infrared spectrometry. The kinetic and equilibrium parameters of the inhibitory interaction of the compounds with guinea-pig heart muscle Na+/K+-ATPase are presented and discussed. Acetylation of the 2 alpha-OH group in gomphogenin or its 3 beta-acetate increases the binding affinity by 15- and 24-fold, respectively, whereas 3 beta-O-acetylation of gomphogenin and its 2 alpha-acetate increases the affinity only two- and threefold. Acetylation of 4'-OH or 3',4'-OH of gomphoside, instead, reduces the high affinity of gomphoside towards Na+/K+-ATPase.

  DOI：

  10.1016/0223-5234(96)88295-x
• 作为产物：
  描述：

  3,4-di-O-benzoyl-6-deoxy-α-D-arabino-hexopyranos-2-ulosyl bromide 在 Rh on carbon molecular sieve 、 氢气 、 四丁基醋酸铵 、 silver carbonate 作用下， 以 甲醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 55.0h， 生成 gomophoside
  参考文献：
  名称：

  一种将2-酮戊二酸双键连接到糖苷二醇上的简洁通用方法：合成高比糖苷和大观霉素。

  摘要：

  DOI：

  10.1002/anie.200500434

文献信息

• Cheung, H.T. Andrew; Chiu, Francis C.K.; Watson, Thomas R., Journal of the Chemical Society. Perkin transactions I, 1986, p. 55 - 60
  作者：Cheung, H.T. Andrew、Chiu, Francis C.K.、Watson, Thomas R.、Wells, Robert J.

  DOI：——

  日期：——
• Cheung, H. T. Andrew; Mutlib, Abdul E.; Watson, Thomas R., Journal of Chemical Research, Miniprint, 1988, # 11, p. 2801 - 2814
  作者：Cheung, H. T. Andrew、Mutlib, Abdul E.、Watson, Thomas R.

  DOI：——

  日期：——
• A Concise and General Method for Doubly Attaching 2-Ketosugars to Aglycon Diols: Synthesis of the Gomphosides and Spectinomycin
  作者：Frieder W. Lichtenthaler、Eckehard Cuny、Osamu Sakanaka

  DOI：10.1002/anie.200500434

  日期：2005.8.5
• Synthesis of acetates of gomphogenin and gomphoside and evaluation of structure-activity relationships
  作者：J Weiland、M Ritzau、R Megges、R Schön、TR Watson、KRH Repke

  DOI：10.1016/0223-5234(96)88295-x

  日期：1995.1

  Acetates of gomphogenin and gomphoside have been synthesized and their structures established by NMR measurements, optical rotation, mass and infrared spectrometry. The kinetic and equilibrium parameters of the inhibitory interaction of the compounds with guinea-pig heart muscle Na+/K+-ATPase are presented and discussed. Acetylation of the 2 alpha-OH group in gomphogenin or its 3 beta-acetate increases the binding affinity by 15- and 24-fold, respectively, whereas 3 beta-O-acetylation of gomphogenin and its 2 alpha-acetate increases the affinity only two- and threefold. Acetylation of 4'-OH or 3',4'-OH of gomphoside, instead, reduces the high affinity of gomphoside towards Na+/K+-ATPase.