2α,5α,9α,10β,14β-pentaacetoxy-taxa-4(20),11-diene

• 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: 2α,5α,9α,10β,14β-pentaacetoxy-taxa-4(20),11-diene
• 英文别名: 2α,5α,9α,10β,14β-pentaacetoxytaxa-4(20),11-diene；[(1S,2S,3R,5S,8R,9R,10R,14S)-2,9,10,14-tetraacetyloxy-8,12,15,15-tetramethyl-4-methylidene-5-tricyclo[9.3.1.03,8]pentadec-11-enyl] acetate
• 化学式: C₃₀H₄₂O₁₀
• 分子量: 562.657
• InChiKey: MDPMMMYRDXOPQH-ZARNYMJHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  40
• 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：
  132
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2α,5α,9α,10β,14β-pentaacetoxy-taxa-4(20),11-diene 在 Abisidia coerulea IFO 4011 、 PDA medium 作用下， 以 乙醇 为溶剂， 反应 168.0h， 以8.5 mg的产率得到14β-hydroxy-2α,5α,9α,10β-tetraacetoxy-taxa-4(20),11-diene
  参考文献：
  名称：

  Combined biotransformations of 4(20),11-taxadienes

  摘要：

  Taxuyunnanine C (1) and its analogs (2 and 3), the C-14 oxygenated 4(20), 11-taxadienes from callus Cultures of Taxus sp., were regio- and stereo-selectively hydroxylated at the 7 beta position by a fungus, Abisidia coerulea IFO 4011, and it was interesting that the longer the alkyl chain of the acyloxyl group at C-14 became, the higher the yield of 7 beta-hydroxylated product was. Besides the three 7 beta-hydroxylated products (5, 9, 17). other nine new products (7, 11, 12, 14, 15, 16, 18, 20 and 21) and six known products (4, 6 8, 10, 13 and 19) were obtained. Subsequently. the acetylated derivatives (24 and 27) of 7 beta- and 9 alpha-hydroxylated products of I were regio- and stereo-specifically hydroxylated at the 9 alpha position by Ginkgo cells and 7 position by A. coerulea, respectively. Thus, the two specific oxidations have been combined. These bioconversions would provide not only valuable intermediates for the semi-synthesis of paclitaxel or other bioactive taxoids front 1 and its analogs. but also some useful hints for the biosynthetic pathway of taxoid in the natural Taxus plant. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.03.136
• 作为产物：
  描述：

  taxuyunnanin C 在 吡啶 、 4-二甲氨基吡啶 、 Abisidia coerulea IFO 4011 、 PDA medium 作用下， 以 乙醇 为溶剂， 反应 175.0h， 生成 2α,5α,9α,10β,14β-pentaacetoxy-taxa-4(20),11-diene
  参考文献：
  名称：

  Combined biotransformations of 4(20),11-taxadienes

  摘要：

  Taxuyunnanine C (1) and its analogs (2 and 3), the C-14 oxygenated 4(20), 11-taxadienes from callus Cultures of Taxus sp., were regio- and stereo-selectively hydroxylated at the 7 beta position by a fungus, Abisidia coerulea IFO 4011, and it was interesting that the longer the alkyl chain of the acyloxyl group at C-14 became, the higher the yield of 7 beta-hydroxylated product was. Besides the three 7 beta-hydroxylated products (5, 9, 17). other nine new products (7, 11, 12, 14, 15, 16, 18, 20 and 21) and six known products (4, 6 8, 10, 13 and 19) were obtained. Subsequently. the acetylated derivatives (24 and 27) of 7 beta- and 9 alpha-hydroxylated products of I were regio- and stereo-specifically hydroxylated at the 9 alpha position by Ginkgo cells and 7 position by A. coerulea, respectively. Thus, the two specific oxidations have been combined. These bioconversions would provide not only valuable intermediates for the semi-synthesis of paclitaxel or other bioactive taxoids front 1 and its analogs. but also some useful hints for the biosynthetic pathway of taxoid in the natural Taxus plant. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.03.136

文献信息

• Combined biotransformations of 4(20),11-taxadienes
  作者：Jungui Dai、Lin Yang、Jun-ichi Sakai、Masayoshi Ando

  DOI：10.1016/j.tet.2005.03.136

  日期：2005.6

  Taxuyunnanine C (1) and its analogs (2 and 3), the C-14 oxygenated 4(20), 11-taxadienes from callus Cultures of Taxus sp., were regio- and stereo-selectively hydroxylated at the 7 beta position by a fungus, Abisidia coerulea IFO 4011, and it was interesting that the longer the alkyl chain of the acyloxyl group at C-14 became, the higher the yield of 7 beta-hydroxylated product was. Besides the three 7 beta-hydroxylated products (5, 9, 17). other nine new products (7, 11, 12, 14, 15, 16, 18, 20 and 21) and six known products (4, 6 8, 10, 13 and 19) were obtained. Subsequently. the acetylated derivatives (24 and 27) of 7 beta- and 9 alpha-hydroxylated products of I were regio- and stereo-specifically hydroxylated at the 9 alpha position by Ginkgo cells and 7 position by A. coerulea, respectively. Thus, the two specific oxidations have been combined. These bioconversions would provide not only valuable intermediates for the semi-synthesis of paclitaxel or other bioactive taxoids front 1 and its analogs. but also some useful hints for the biosynthetic pathway of taxoid in the natural Taxus plant. (c) 2005 Elsevier Ltd. All rights reserved.

表征谱图