13α-acetyl-4α,20-dihydroxybrevifoliol | 708212-80-0

• 英文名称: 13α-acetyl-4α,20-dihydroxybrevifoliol
• 英文别名: [(2S,4R,5R,5aS,6S,8S,9S,9aS,10aS)-2,5,6-triacetyloxy-8,9-dihydroxy-9-(hydroxymethyl)-10a-(2-hydroxypropan-2-yl)-3,5a-dimethyl-2,4,5,6,7,8,9a,10-octahydro-1H-benzo[g]azulen-4-yl] benzoate
• CAS: 708212-80-0
• 化学式: C₃₃H₄₄O₁₂
• 分子量: 632.705
• InChiKey: LFYUCOHNDPARQP-CNZIXFJUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  45
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  186
• 氢给体数：
  4
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  13α-acetyl-4α,20-dihydroxybrevifoliol 在 吡啶 、 咪唑 、 3 A molecular sieve 、 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 42.0h， 生成 13α-acetyl-20-tert-butyldimethylsilyloxy-5-methanesulfonyl-4α-hydroxybrevifoliol
  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 四氧化锇 、 N-甲基吗啉氧化物 作用下， 以 丙酮 、 叔丁醇 为溶剂， 以72%的产率得到13α-acetyl-4α,20-dihydroxybrevifoliol
  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