14β-hydroxy-5α,7β,9α,10β,13α-pentaacetoxy-4(20),11-taxadiene | 189104-61-8

• 英文名称: 14β-hydroxy-5α,7β,9α,10β,13α-pentaacetoxy-4(20),11-taxadiene
• 英文别名: [(1S,3R,5S,7S,8S,9R,10R,13R,14R)-7,9,10,13-tetraacetyloxy-14-hydroxy-8,12,15,15-tetramethyl-4-methylidene-5-tricyclo[9.3.1.03,8]pentadec-11-enyl] acetate
• CAS: 189104-61-8
• 化学式: C₃₀H₄₂O₁₁
• 分子量: 578.657
• InChiKey: QELFDGCFNKOHPZ-DPAUGTDCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  41
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  152
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 14β-hydroxy-5α,7β,9α,10β,13α-pentaacetoxy-4(20),11-taxadiene 生成 Acetic acid (1S,3R,5S,7S,8S,9R,10R,13R,14R)-5,7,10,13,14-pentaacetoxy-8,12,15,15-tetramethyl-4-methylene-tricyclo[9.3.1.0^3,8]pentadec-11-en-9-yl ester
  参考文献：
  名称：

  Selective microbial hydroxylation and biological rearrangement of taxoids

  摘要：

  5 alpha,7 beta,9 alpha,10 beta, 13 alpha-Pentaacetoxy-4(20),11-taxadiene 1 was selectively transformed into its 1 beta,14 beta-hydroxylated derivatives 2, 3, and 11(15-->1)abeotaxane 4 by different filamentous fungi. Microbial transformation of a series of taxoids with a 4(20) exocyclic double bond was described. The microbial enzymatic systems may be served as a useful tool to mimic some steps of taxoid biosynthesis in Taxus spp.. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00453-x
• 作为产物：
  描述：

  5α,7β,9α,10β,13α-pentaacetoxy-4(20),11(12)-taxadiene 反应 120.0h， 以39%的产率得到Acetic acid (1S,3R,5S,7S,8S,9R,10R,13S)-5,7,10,13-tetraacetoxy-1-hydroxy-8,12,15,15-tetramethyl-4-methylene-tricyclo[9.3.1.0^3,8]pentadec-11-en-9-yl ester
  参考文献：
  名称：

  Selective microbial hydroxylation and biological rearrangement of taxoids

  摘要：

  5 alpha,7 beta,9 alpha,10 beta, 13 alpha-Pentaacetoxy-4(20),11-taxadiene 1 was selectively transformed into its 1 beta,14 beta-hydroxylated derivatives 2, 3, and 11(15-->1)abeotaxane 4 by different filamentous fungi. Microbial transformation of a series of taxoids with a 4(20) exocyclic double bond was described. The microbial enzymatic systems may be served as a useful tool to mimic some steps of taxoid biosynthesis in Taxus spp.. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00453-x

文献信息

• Reanalysis of the biotransformation of 4(20),11(12)-taxadiene derivatives
  作者：Di-An Sun、Françoise Sauriol、Orval Mamer、Lolita O Zamir

  DOI：10.1139/v01-125

  日期：2001.9.1

  Reanalysis of the biotransformation of 4(20),11(12)-taxadiene derivatives by Absidia coerulea ATCC 10738a unravelled additional unprecedented rearrangement reactions. 5α,7β,9α,10β,13α-pentaacetoxy-4(20),11(12)-taxadiene (1) was converted to 10 new minor taxane derivatives in addition to the previously reported C-1, C-14-hydroxylations and C-15-hydroxylated abeo-taxane. In addition, 2-deacetoxytaxinine J (2) was successfully metabolized with the same fungi.Key words: natural products, terpenes and terpenoids, microorganism, oxygenation, rearrangement.

  Absidia coerulea ATCC 10738a重新分析了4（20），11（12）-紫杉烯衍生物的生物转化，揭示了额外的前所未有的重排反应。5α，7β，9α，10β，13α-五乙酰氧基-4（20），11（12）-紫杉烯（1）被转化为10个新的次要紫杉烷衍生物，除了先前报道的C-1，C-14-羟基化和C-15-羟基化的abeo-紫杉烷。此外，2-去乙酰基紫杉烷J（2）也成功地被同一种真菌代谢。关键词：天然产物，萜类化合物，微生物，氧化，重排。