10-deacetylpaclitaxel | 162809-94-1

• 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: 10-deacetylpaclitaxel
• 英文别名: [(1S,2S,3R,4S,7R,9S,10S,12S,15S)-4-acetyloxy-15-[(2R,3S)-3-benzamido-2-hydroxy-3-phenylpropanoyl]oxy-1,9,12-trihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate
• CAS: 162809-94-1
• 化学式: C₄₅H₄₉NO₁₃
• 分子量: 811.883
• InChiKey: TYLVGQKNNUHXIP-XTSAHDJPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  59
• 可旋转键数：
  12
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  215
• 氢给体数：
  5
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  10-deacetylpaclitaxel 在 4-二甲氨基吡啶 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.33h， 生成 7-chloroacetyl-10-deacetylpaclitaxel
  参考文献：
  名称：

  SELECTIVE CONVERSION OF 2′,7-BIS-MONOCHLOROACETYLPACLITAXEL ANALOGS TO 7-MONOCHLOROACETYL DERIVATIVES BY SOLVOLYSIS IN METHANOL

  摘要：

  2',7-bis-Monochloroacetylpaclitaxel analogs can be conveniently converted to their corresponding 7-monochloroacetyl derivatives by allowing dilute methanolic solutions to stand at ambient temperature for 48 h.

  DOI：

  10.1081/scc-120006037
• 作为产物：
  描述：

  2'-O-TBDMS-7-O-TES-9,10-diketo-paclitaxel 在 sodium tetrahydroborate 、 氟化氢吡啶 作用下， 以 吡啶 、 乙醇 为溶剂， 反应 4.25h， 生成 10-deacetylpaclitaxel
  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

文献信息

• Syntheses of novel C-9 and C-10 modified bioactive taxanes
  作者：Apurba Datta、David G. Vander Velde、Gunda I. Georg、Richard H. Himes

  DOI：10.1016/0040-4039(95)00208-t

  日期：1995.3

  A method has been developed for the syntheses of hitherto unreported C-9 and C-10 modified taxanes. These analogs demonstrated excellent to good cytotoxicity against B 16 melanoma cells.

  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。