[(1S,2S,4S,7R,9S,10S,12R,13S,16R)-4,7,13-triacetyloxy-2,12-dihydroxy-5,9,17,17-tetramethyl-8-oxo-15-oxatetracyclo[7.6.1.12,6.013,16]heptadec-5-en-10-yl] acetate | 143536-90-7

• 英文名称: [(1S,2S,4S,7R,9S,10S,12R,13S,16R)-4,7,13-triacetyloxy-2,12-dihydroxy-5,9,17,17-tetramethyl-8-oxo-15-oxatetracyclo[7.6.1.12,6.013,16]heptadec-5-en-10-yl] acetate
• CAS: 143536-90-7
• 化学式: C₂₈H₃₈O₁₂
• 分子量: 566.603
• InChiKey: WVZDBBOSFOZTDY-XWRVRYBQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  40
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  172
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  [(1S,2S,4S,7R,9S,10S,12R,13S,16R)-4,7,13-triacetyloxy-2,12-dihydroxy-5,9,17,17-tetramethyl-8-oxo-15-oxatetracyclo[7.6.1.12,6.013,16]heptadec-5-en-10-yl] acetate 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 以87%的产率得到
  参考文献：
  名称：

  The chemistry of taxanes: unexpected rearrangement of baccatin III during chemoselective debenzoylation with Bu3SnOMe/LiCl

  摘要：

  Chemoselective debenzoylation of 7,13-diacetyl baccatin III was achieved with tributyltin methoxide in NMP in the presence of lithium chloride as an activating agent. Surprisingly, the debenzoylation reaction was followed by rapid intramolecular cleavage of the oxetane ring to produce a novel taxane structure featuring a tetrahydrofuran ring.

  DOI：

  10.1016/0040-4039(92)88078-j
• 作为产物：
  描述：

  7,13-diacetylbaccatin III 在 B₃SnOCH₃ 、 lithium chloride 作用下， 以 various solvent(s) 为溶剂， 反应 2.0h， 以67%的产率得到[(1S,2S,4S,7R,9S,10S,12R,13S,16R)-4,7,13-triacetyloxy-2,12-dihydroxy-5,9,17,17-tetramethyl-8-oxo-15-oxatetracyclo[7.6.1.12,6.013,16]heptadec-5-en-10-yl] acetate
  参考文献：
  名称：

  The chemistry of taxanes: unexpected rearrangement of baccatin III during chemoselective debenzoylation with Bu3SnOMe/LiCl

  摘要：

  Chemoselective debenzoylation of 7,13-diacetyl baccatin III was achieved with tributyltin methoxide in NMP in the presence of lithium chloride as an activating agent. Surprisingly, the debenzoylation reaction was followed by rapid intramolecular cleavage of the oxetane ring to produce a novel taxane structure featuring a tetrahydrofuran ring.

  DOI：

  10.1016/0040-4039(92)88078-j