(3S,5S,6R,8S,9R,10S,13R,14S,15S,17R)-17-((E)-(R)-4-Hydroxy-1,5-dimethyl-hex-2-enyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthrene-3,6,8,15-tetraol | 105377-89-7

• 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: (3S,5S,6R,8S,9R,10S,13R,14S,15S,17R)-17-((E)-(R)-4-Hydroxy-1,5-dimethyl-hex-2-enyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthrene-3,6,8,15-tetraol
• 英文别名: (22e)-5alpha-Cholest-22-ene-3beta,6beta,8,15alpha,24-pentaol；(3S,5S,6R,8S,9R,10S,13R,14S,15S,17R)-17-[(E,2R)-5-hydroxy-6-methylhept-3-en-2-yl]-10,13-dimethyl-1,2,3,4,5,6,7,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-3,6,8,15-tetrol
• CAS: 105377-89-7
• 化学式: C₂₇H₄₆O₅
• 分子量: 450.659
• InChiKey: SKNLGWKCGJLAJY-GFZNIXJRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  101
• 氢给体数：
  5
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (22E)-5α-Cholest-22-ene-3β,6β,8,15α,24-pentol,15-sulphate 在 吡啶 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 生成 (3S,5S,6R,8S,9R,10S,13R,14S,15S,17R)-17-((E)-(R)-4-Hydroxy-1,5-dimethyl-hex-2-enyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthrene-3,6,8,15-tetraol
  参考文献：
  名称：

  Starfish Saponins XXX. Isolation of Sixteen Steroidal Glycosides and Three Polyhydroxysteroids from the Mediterranean Starfish Coscinasterias Tenuispina

  摘要：

  AbstractSixteen steroidal glycosides have been isolated from the starfish Coscinasterias tenuispina. The more polar components are the “asterosaponins” 1A–1E, 2A–2C, 3E and 3G, consisting of a Δ9(11)‐3β,6α‐dihydroxysteroidal moiety, a pentasaccharide portion attached at C‐6 and a sulphate group at C‐3. Compounds 1C, 2C and 1D are new saponins assigned as the tenuispinoside A through C. The second group of polar glycosides consists of two new xylose saponins, possessing monosulphate polyhydroxysteroidal aglycones and two new 4‐O‐sulphated glucose saponins, assigned as the coscinasteroside A through D (4–2). The less polar glycosides are the new “non‐sulphated” xylosides 8 and 9, designed as coscinasterosides E and F.The structures of the new saponins were determined by extensive 1H and 13C NMR investigations, FAB mass spectroscopy, and by comparison with known compounds. The location of the sulphate ester functionalities in 4–7 were assigned on comparison of their spectral data with those of the corresponding desulphated analogues. C. tenuispina also contains three new monosulphated polyhydroxysteroids, which were assigned the structures 10 to 12.

  DOI：

  10.1002/bscb.19860950912