13α-acetoxy-5α-cinnamoyloxy-2α-(methoxymethoxy)taxa-4(20),11-diene-9α,10β-diol | 477894-70-5

• 英文名称: 13α-acetoxy-5α-cinnamoyloxy-2α-(methoxymethoxy)taxa-4(20),11-diene-9α,10β-diol
• 英文别名: [(1R,2R,3R,5S,8R,9R,10R,13S)-13-acetyloxy-9,10-dihydroxy-2-(methoxymethoxy)-8,12,15,15-tetramethyl-4-methylidene-5-tricyclo[9.3.1.03,8]pentadec-11-enyl] (E)-3-phenylprop-2-enoate
• CAS: 477894-70-5
• 化学式: C₃₃H₄₄O₈
• 分子量: 568.708
• InChiKey: QVADMPJYSRCPQQ-UARSWVRWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  41
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  13α-acetoxy-5α-cinnamoyloxy-2α-(methoxymethoxy)taxa-4(20),11-diene-9α,10β-diol 在 吡啶 、 盐酸 、 4-二甲氨基吡啶 作用下， 以 异丙醇 为溶剂， 反应 7.0h， 生成 taxezopidine G
  参考文献：
  名称：

  An Efficient Conversion of Taxinine to Taxinine NN-1, an Anticancer Agent and a Modulator of Multidrug-Resistant Tumor Cells

  摘要：

  Taxinine NN-1 (1), which shows significant activities as a modulator of multidrug-resistant cancer cells and as an anticancer agent in an in vitro assay based on a HCC panel, was synthesized in order to obtain sufficient material for a higher order bioassay from easily available taxinine (2). The synthesis was achieved via intermediate 8, which was derived from 2 by the stepwise protection of a 9, 10-dihydroxyl group as acetonide and a 2-hydroxyl group as a MOM protecting group. The temporary elimination of a cinnamoyl group at C-5 of 8 and successive reduction of a C-13 carbonyl group of the resulting 9 gave 10 and the undesired 13-epimer 11. The latter was recycled to 9 by oxidation with MnO2. Stepwise acetylation and cinnamoylation at C-13 and C-5 of 10 and successive deprotection of the acetonide protecting group at C-9,10 of the resulting 13 gave diol 14. Diacetylation of 14 and deprotection of the MOM protecting group at C-2 of the resulting 15 gave 1. The overall yield of 1 was 45% in 11 steps from 2.

  DOI：

  10.1021/np020240n
• 作为产物：
  描述：

  13α-acetoxy-9α,10β-(dimethylmethylenedioxy)-2α-(methoxymethoxy)taxa-4(20),11-dien-5α-ol 在 吡啶 、 4-二甲氨基吡啶 、 溶剂黄146 作用下， 反应 24.0h， 生成 13α-acetoxy-5α-cinnamoyloxy-2α-(methoxymethoxy)taxa-4(20),11-diene-9α,10β-diol
  参考文献：
  名称：

  An Efficient Conversion of Taxinine to Taxinine NN-1, an Anticancer Agent and a Modulator of Multidrug-Resistant Tumor Cells

  摘要：

  Taxinine NN-1 (1), which shows significant activities as a modulator of multidrug-resistant cancer cells and as an anticancer agent in an in vitro assay based on a HCC panel, was synthesized in order to obtain sufficient material for a higher order bioassay from easily available taxinine (2). The synthesis was achieved via intermediate 8, which was derived from 2 by the stepwise protection of a 9, 10-dihydroxyl group as acetonide and a 2-hydroxyl group as a MOM protecting group. The temporary elimination of a cinnamoyl group at C-5 of 8 and successive reduction of a C-13 carbonyl group of the resulting 9 gave 10 and the undesired 13-epimer 11. The latter was recycled to 9 by oxidation with MnO2. Stepwise acetylation and cinnamoylation at C-13 and C-5 of 10 and successive deprotection of the acetonide protecting group at C-9,10 of the resulting 13 gave diol 14. Diacetylation of 14 and deprotection of the MOM protecting group at C-2 of the resulting 15 gave 1. The overall yield of 1 was 45% in 11 steps from 2.

  DOI：

  10.1021/np020240n