7β-hydroxy-2α,5α,10β,14β-tetraacetoxytaxa-4(20),11-diene | 221053-30-1

• 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: 7β-hydroxy-2α,5α,10β,14β-tetraacetoxytaxa-4(20),11-diene
• 英文别名: 2α,5α,10β,14β-tetraacetoxytaxa-4(20),11-diene-7β-ol；[(1S,2S,3R,5S,7S,8S,10S,14S)-2,10,14-triacetyloxy-7-hydroxy-8,12,15,15-tetramethyl-4-methylidene-5-tricyclo[9.3.1.03,8]pentadec-11-enyl] acetate
• CAS: 221053-30-1
• 化学式: C₂₈H₄₀O₉
• 分子量: 520.62
• InChiKey: UCZNNEIDEURDED-FPOKQUGOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  125
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  7β-hydroxy-2α,5α,10β,14β-tetraacetoxytaxa-4(20),11-diene 在 2,4-二氯苯氧乙酸 、 6-苄氨基嘌呤 Ginkgo biloba L 、 MS medium 、 naphthalene acetic acid 作用下， 以 乙醇 为溶剂， 反应 144.0h， 以2.0 mg的产率得到7β,10β-dihydroxy-2α,5α,14β-triacetoxy-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 Absidia coerulea IFO 4011 作用下， 反应 168000.0h， 以5%的产率得到7β-hydroxy-2α,5α,10β,14β-tetraacetoxytaxa-4(20),11-diene
  参考文献：
  名称：

  Specific oxidation of C-14 oxygenated 4(20),11-taxadienes by microbial transformation

  摘要：

  Three C-14 oxygenated taxanes, 2alpha,5alpha,10beta,14beta-tetraacetoxytaxa-4(20),11-diene (1), 2alpha,5alpha,10beta-triacetoxy-14beta-(2-methyl-butyryloxy)taxa-4(20),11-diene (2), and yunanaxane (3), major products of callus cultures of Taxus spp., were regio- and stereoselectively hydroxylated at the 7beta position by a fungus, Absidia coerulea IFO 4011. Intriguingly, when 1 was co-administered with beta-cyclodextrin and incubated with the fungus cell cultures, three other compounds 5alpha,9alpha,10beta,13alpha-tetraacetoxytaxa-4(20),11-dien-14beta-ol (7), 5alpha,9alpha,10beta,13alpha-tetraacetoxytaxa-4(20),11-dien-1beta-ol (8) and 5alpha,9alpha,10beta,13alpha-tetraacetoxy-11(15-->1) abeotaxa-4(20), 11-dien-15-ol (9) were obtained. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02714-4

文献信息

• Specific oxidation of C-14 oxygenated 4(20),11-taxadienes by microbial transformation
  作者：Jungui Dai、Shujun Zhang、Jun-ichi Sakai、Jiao Bai、Yoshiki Oku、Masayoshi Ando

  DOI：10.1016/s0040-4039(02)02714-4

  日期：2003.1

  Three C-14 oxygenated taxanes, 2alpha,5alpha,10beta,14beta-tetraacetoxytaxa-4(20),11-diene (1), 2alpha,5alpha,10beta-triacetoxy-14beta-(2-methyl-butyryloxy)taxa-4(20),11-diene (2), and yunanaxane (3), major products of callus cultures of Taxus spp., were regio- and stereoselectively hydroxylated at the 7beta position by a fungus, Absidia coerulea IFO 4011. Intriguingly, when 1 was co-administered with beta-cyclodextrin and incubated with the fungus cell cultures, three other compounds 5alpha,9alpha,10beta,13alpha-tetraacetoxytaxa-4(20),11-dien-14beta-ol (7), 5alpha,9alpha,10beta,13alpha-tetraacetoxytaxa-4(20),11-dien-1beta-ol (8) and 5alpha,9alpha,10beta,13alpha-tetraacetoxy-11(15-->1) abeotaxa-4(20), 11-dien-15-ol (9) were obtained. (C) 2003 Elsevier Science Ltd. All rights reserved.
• 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.