2'-TBS-10-epi-7-TES-paclitaxel | 162809-92-9

• 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: 2'-TBS-10-epi-7-TES-paclitaxel
• CAS: 162809-92-9
• 化学式: C₅₉H₇₉NO₁₄Si₂
• 分子量: 1082.45
• InChiKey: VEWXDDANFBFDEA-HWSJCRGOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.79
• 重原子数：
  76.0
• 可旋转键数：
  17.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  199.29
• 氢给体数：
  2.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  2'-TBS-10-epi-7-TES-paclitaxel 在 吡啶 、 氟化氢吡啶 作用下， 以79%的产率得到10-epi-paclitaxel
  参考文献：
  名称：

  新型C-9和C-10修饰的生物活性紫杉烷的合成

  摘要：

  已经开发了一种用于合成迄今未报道的C-9和C-10修饰的紫杉烷的方法。这些类似物对B 16黑色素瘤细胞表现出优异的细胞毒性。

  DOI：

  10.1016/0040-4039(95)00208-t
• 作为产物：
  描述：

  10-deacetyl-2'-(tert-butyldimethylsilyl)-7-(triethylsilyl) paclitaxel 在 吡啶 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 N-甲基吲哚酮 、 四丙基高钌酸铵 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 6.25h， 生成 2'-TBS-10-epi-7-TES-paclitaxel
  参考文献：
  名称：

  The Chemistry of the Taxane Diterpene:  Stereoselective Reductions of Taxanes

  摘要：

  Stereoselective reductions of taxanes are detailed. Chelation-controlled reductions employing SmI2 are described for the stereoselective reduction of the 9-keto functionality of the diterpene moiety of several taxanes. In all cases the 9 beta-hydroxy stereochemistry was obtained exclusively. In addition to C9 reduction, partial C10-deoxygenation via beta-elimination was observed. Lower reaction temperatures favored the reduction pathway without beta-elimination. Acetic acid as the proton source gave higher yields and cleaner reaction products. This chemistry provided access to taxanes with 9 beta-hydroxy, 10 beta-hydroxy stereochemistry. Evidence is presented, suggesting that chelation of samarium with the 7 beta-hydroxyl group is required for the reduction of the C9 ketone moiety. The synthesis of paclitaxel analogues, possessing the 9 alpha-hydroxy, 10 alpha-hydroxy stereochemistry was also achieved. Reduction of the 10-ketone group of 10-oxopaclitaxel employing NaBH4 produced 10-deacetyl-10-epipaclitaxel stereoselectively. Using an excess of NaBH4 in this reaction gave exclusively the 9 alpha-hydroxy, 10 alpha-hydroxy paclitaxel analogue.

  DOI：

  10.1021/jo981194s