7,9-acetonide 13-acetyl-9-dihydrobaccatin III | 148584-51-4

• 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: 7,9-acetonide 13-acetyl-9-dihydrobaccatin III
• 英文别名: 9(R)-dihydro-7,9-isopropylidene-baccatin-III；9-dihydrobaccatin III 7,9-acetonide；7,9 acetonide 9-DHB；[(1R,2S,5R,7S,11R,12R,15S,17S,18S,19S)-2,12-diacetyloxy-15,17-dihydroxy-9,9,14,19,20,20-hexamethyl-4,8,10-trioxapentacyclo[9.7.1.113,17.02,5.07,19]icos-13-en-18-yl] benzoate
• CAS: 148584-51-4
• 化学式: C₃₄H₄₄O₁₁
• 分子量: 628.717
• InChiKey: XALVZJNHOBEJMX-JZNYTDQOSA-N

物化性质

• 沸点：
  691.8±55.0 °C(predicted)
• 密度：
  1.33±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  45
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  147
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  7,9-acetonide 13-acetyl-9-dihydrobaccatin III 在 jones' reagent 作用下， 反应 1.0h， 以85%的产率得到[(1R,2S,5R,7S,11R,12R,17S,18S,19S)-2,12-diacetyloxy-17-hydroxy-9,9,14,19,20,20-hexamethyl-15-oxo-4,8,10-trioxapentacyclo[9.7.1.113,17.02,5.07,19]icos-13-en-18-yl] benzoate
  参考文献：
  名称：

  加拿大红豆杉中主要紫杉烷的重排

  摘要：

  研究了来自加拿大红豆杉的主要紫杉烷9-二氢-13-乙酰浆果赤霉素III的重排。报道了两种新的环化产物以及一种新型的降解化合物。它们的结构是通过光谱技术确定的。

  DOI：

  10.1016/s0040-4039(99)01577-4
• 作为产物：
  描述：

  9(R)-dihydro-7,9-isopropylidene-13-acetylbaccatin-III 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 phosphate buffer 为溶剂， 反应 7.0h， 以60%的产率得到7,9-acetonide 13-acetyl-9-dihydrobaccatin III
  参考文献：
  名称：

  加拿大红豆杉中主要紫杉烷的重排

  摘要：

  研究了来自加拿大红豆杉的主要紫杉烷9-二氢-13-乙酰浆果赤霉素III的重排。报道了两种新的环化产物以及一种新型的降解化合物。它们的结构是通过光谱技术确定的。

  DOI：

  10.1016/s0040-4039(99)01577-4

文献信息

• [EN] TAXANE AND ABEO-TAXANE ANALOGS<br/>[FR] ANALOGUES DU TAXANE ET DE L'ABÉO-TAXANE
  申请人：ARBOR THERAPEUTICS LLC

  公开号：WO2013106029A1

  公开（公告）日：2013-07-18

  The present application discloses new taxane analogs, intermediates and methods for producing them. The present application is also directed to pharmaceutical formulations comprising abeo-taxanes and methods of treating cancer with the abeo-taxanes.

  本申请公开了新的紫杉醇类似物、中间体以及生产它们的方法。本申请还涉及包含阿贝奥紫杉醇的药物配方以及使用阿贝奥紫杉醇治疗癌症的方法。
• An Efficient Synthesis of the Taxane-Derived Anticancer Agent ABT-271
  作者：John A. DeMattei、M. Robert Leanna、Wenke Li、Paul J. Nichols、Michael W. Rasmussen、Howard E. Morton

  DOI：10.1021/jo0057203

  日期：2001.5.1

  ABT-271, 1, has been identified as a promising anticancer agent. ABT-271 is a novel taxane possessing a CS-(R)-hydroxyl group as opposed to a CS-ketone which is present in Taxol and Taxotere. To further evaluate ABT-271 as a potential anticancer agent, an efficient synthesis was developed which allows the large scale synthesis of ABT-271. Ketalization of the 7,9-diol of 9-DHAB-III, 2, allows selective removal of th:e CI-acetate with phenyllithium. The resulting C13-hydroxyl group is then acylated using LiHMDS and beta -lactam 22 to give ABT-271 in protected form. The protecting groups were removed first by acidic hydrolysis followed by basic hydrolysis to provide ABT-271. Application of this synthetic sequence provided over 600 g of ABT-271, 1.
• Synthesis of 9-dihydrotaxol: A novel bioactive taxane
  作者：Larry L. Klein

  DOI：10.1016/s0040-4039(00)60342-8

  日期：1993.3

  The synthesis of 9-dihydrotaxol (8) is described via a novel deacylation reaction. This analog exhibits increased activity in the microtubule assay.
• Antitumor Activity of 9(R)-Dihydrotaxane Analogs
  作者：Larry L. Klein、Leping Li、Clarence J. Maring、Clinton M. Yeung、Sheela A. Thomas、David J. Grampovnik、Jacob J. Plattner

  DOI：10.1021/jm00009a009

  日期：1995.4

  A novel reduced taxane, 13-acetyl-9(R)-dihydrobaccatin III (1) has been isolated from Taxus canadensis. The selective C-13 deacetylation of this isolate has allowed for the preparation of a wide variety of 9(R)-dihydrotaxane analogs. In general, this series has shown greater stability and water solubility than the 9-carbonyl series while retaining antimicrotubule and tumor cell cytotoxicity activities relative to taxol. Placement of polar functionalities at the C-7 position results in loss of activity whereas alkylation or acylation of either C-7 or C-9 hydroxyl groups ameliorate the activity.
• US8912229B2
  申请人：——

  公开号：US8912229B2

  公开（公告）日：2014-12-16