(25R)-3β-(benzyloxy)-5α-spirostan-6β-ol | 210687-09-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (25R)-3β-(benzyloxy)-5α-spirostan-6β-ol
• 英文别名: (1R,2S,4S,5'R,6R,7S,8R,9S,12S,13R,16S,18S,19R)-5',7,9,13-tetramethyl-16-phenylmethoxyspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-19-ol
• CAS: 210687-09-5
• 化学式: C₃₄H₅₀O₄
• 分子量: 522.769
• InChiKey: QWJGCDYOGCVWBO-GLQUNUKKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  38
• 可旋转键数：
  3
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (25R)-3β-(benzyloxy)-5α-spirostan-6β-ol 在 盐酸 、 amalgamated zinc 、 重铬酸吡啶 、 四(三苯基膦)钯 、 三正丁基氢锡 、 四丁基碘化铵 、 sodium hydride 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 lithium chloride 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 38.1h， 生成 [(2R,6R)-6-((3S,5S,6R,8R,9S,10R,13R,14S,17S)-3,6-Bis-benzyloxy-10,13-dimethyl-2,3,4,5,6,7,8,9,10,11,12,13,14,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-2-methyl-heptyloxy]-tert-butyl-dimethyl-silane
  参考文献：
  名称：

  Synthesis of (25R)-5α-Cholestane-3β,6β,15α,16β,26-pentol, a Cytostatic Starfish Steroid

  摘要：

  The synthesis of (25R)-5 alpha-cholestane-3 beta,6 beta, 15 alpha,16 beta,26-pentol (1a), a marine cytostatic steroid, has been achieved in 13 steps (7.8% overall yield) starting from commercially available diosgenin (2). A key step in the synthesis was the dimethyldioxirane oxidation of the enolsilane 16 to introduce the 15 alpha-hydroxy group in the D ring.

  DOI：

  10.1021/jo980266c
• 作为产物：
  描述：

  薯蓣皂素 在 sodium hydroxide 、 lithium aluminium tetrahydride 、 重铬酸吡啶 、 dimethyl sulfide borane 、 双氧水 、 四丁基碘化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 39.3h， 生成 (25R)-3β-(benzyloxy)-5α-spirostan-6β-ol
  参考文献：
  名称：

  Synthesis of (25R)-5α-Cholestane-3β,6β,15α,16β,26-pentol, a Cytostatic Starfish Steroid

  摘要：

  The synthesis of (25R)-5 alpha-cholestane-3 beta,6 beta, 15 alpha,16 beta,26-pentol (1a), a marine cytostatic steroid, has been achieved in 13 steps (7.8% overall yield) starting from commercially available diosgenin (2). A key step in the synthesis was the dimethyldioxirane oxidation of the enolsilane 16 to introduce the 15 alpha-hydroxy group in the D ring.

  DOI：

  10.1021/jo980266c

文献信息

• Structure–activity relationships of saponin derivatives: A series of entry inhibitors for highly pathogenic H5N1 influenza virus
  作者：Ning Ding、Qing Chen、Wei Zhang、Sumei Ren、Ying Guo、Yingxia Li

  DOI：10.1016/j.ejmech.2012.04.022

  日期：2012.7

  The occurrence of highly pathogenic avian influenza virus H5N1 highlights the urgent need for new classes of antiviral drugs. Theoretically, each of steps in influenza viral life cycle can be a target of antiviral therapeutics. However, up to date, no licenced entry inhibitor drug is available for H5N1 or any other influenza viruses. Our strategy for developing new anti-influenza therapeutics is to target the interaction between HA and sialic acid which is influenza viral receptor presented on host cell surface. Here, based on our previously discovered small molecule inhibitor saponin 1, intensive SAR studies around the sugar chain and aglycone were conducted. The results showed that both the chacotriosyl residue and the chlorogenin moiety of active compound 1 are important for the antiviral activity, although several subtle modifications can be made on particular positions. (C) 2012 Elsevier Masson SAS. All rights reserved.