13α-acetyl-4α,20-dihydroxy-5-methanesulfonylhydroxybrevifoliol | 708212-82-2

• 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: 13α-acetyl-4α,20-dihydroxy-5-methanesulfonylhydroxybrevifoliol
• 英文别名: [(2S,4R,5R,5aS,6S,8S,9S,9aS,10aS)-2,5,6-triacetyloxy-9-hydroxy-9-(hydroxymethyl)-10a-(2-hydroxypropan-2-yl)-3,5a-dimethyl-8-methylsulfonyloxy-2,4,5,6,7,8,9a,10-octahydro-1H-benzo[g]azulen-4-yl] benzoate
• CAS: 708212-82-2
• 化学式: C₃₄H₄₆O₁₄S
• 分子量: 710.797
• InChiKey: RSLHQKHECAVGPH-PEQYYCHYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  49
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  218
• 氢给体数：
  3
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  13α-acetyl-4α,20-dihydroxy-5-methanesulfonylhydroxybrevifoliol 在 四丁基醋酸铵 作用下， 以 丁酮 为溶剂， 反应 19.0h， 以44%的产率得到[(1S,3S,5S,8R,9R,10S,11S,13R,16S)-5,9,11-triacetyloxy-16-hydroxy-3-(2-hydroxypropan-2-yl)-6,10-dimethyl-14-oxatetracyclo[8.6.0.03,7.013,16]hexadec-6-en-8-yl] benzoate
  参考文献：
  名称：

  Characterization of an abeo-Taxane:  Brevifoliol and Derivatives

  摘要：

  Brevifoliol is a natural diterpene isolated from Taxus baccata Nutt. A series of brevifoliol 1 derivatives, 2-8 and 10, were prepared for characterization and semisynthesis purposes and included the introduction of acetyl, Troc, and TES groups at C-5 and C-13. Derivatives 16-20 of 5-acetylbrevifoliol 2 were obtained via esterification with cinnamic acid, with both 2S-(-)- and 2R-(+)-3-phenyllactic acid, and with N-benzoyl(2'R,3'S)-3'-phenylisoserine at C-13. Brevifoliol compounds 12, 13, and 15 with either 2S-(-)-phenyllactate moieties at C-5 and C-13 or an N-benzoyl-(2'R,3'S)-3'-phenylisoserinyl at C-13 were also prepared. An abeo-taxane structure for 1 was clearly defined from the C-13 NMR analysis of the 5-acetyl-13-oxo derivative 8 and from the conversion of 1 into 10, a conformationally restrained compound having a C-13, C-15 oxygen bridge. The biological activity of each of these derivatives is being studied.

  DOI：

  10.1021/np0304565
• 作为产物：
  描述：

  10β-benzoxy-1β,5α-dihydroxy-7β,9α,13α-triacetoxy-11(15->1)-abeotaxa-4(20),11-diene 在 吡啶 、 咪唑 、 四氧化锇 、 3 A molecular sieve 、 4 A molecular sieve 、 四丁基氟化铵 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 、 叔丁醇 为溶剂， 反应 42.0h， 生成 13α-acetyl-4α,20-dihydroxy-5-methanesulfonylhydroxybrevifoliol
  参考文献：
  名称：

  Characterization of an abeo-Taxane:  Brevifoliol and Derivatives

  摘要：

  Brevifoliol is a natural diterpene isolated from Taxus baccata Nutt. A series of brevifoliol 1 derivatives, 2-8 and 10, were prepared for characterization and semisynthesis purposes and included the introduction of acetyl, Troc, and TES groups at C-5 and C-13. Derivatives 16-20 of 5-acetylbrevifoliol 2 were obtained via esterification with cinnamic acid, with both 2S-(-)- and 2R-(+)-3-phenyllactic acid, and with N-benzoyl(2'R,3'S)-3'-phenylisoserine at C-13. Brevifoliol compounds 12, 13, and 15 with either 2S-(-)-phenyllactate moieties at C-5 and C-13 or an N-benzoyl-(2'R,3'S)-3'-phenylisoserinyl at C-13 were also prepared. An abeo-taxane structure for 1 was clearly defined from the C-13 NMR analysis of the 5-acetyl-13-oxo derivative 8 and from the conversion of 1 into 10, a conformationally restrained compound having a C-13, C-15 oxygen bridge. The biological activity of each of these derivatives is being studied.

  DOI：

  10.1021/np0304565