9(R)-dihydro-7,9-isopropylidene-13-acetylbaccatin-III | 148584-49-0

• 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: 9(R)-dihydro-7,9-isopropylidene-13-acetylbaccatin-III
• 英文别名: 7,9-acetonide 13-acetyl-9-dihydrobaccatin III；7,9 acetonide 9-DHB；[(1R,2S,5R,7S,11R,12R,15S,17S,18S,19S)-2,12,15-triacetyloxy-17-hydroxy-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: 148584-49-0
• 化学式: C₃₆H₄₆O₁₂
• 分子量: 670.754
• InChiKey: YRLKTJGNSBXDDH-BHISGFMXSA-N

物化性质

• 沸点：
  691.3±55.0 °C(predicted)
• 密度：
  1.31±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  48
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  153
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  9(R)-dihydro-7,9-isopropylidene-13-acetylbaccatin-III 在 sodium tetrahydroborate 、 jones' reagent 、 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 、 phosphate buffer 为溶剂， 反应 8.0h， 生成 [(1S,2R,3S,6R,8S,9S,10R,11R,16S)-8,11,16-trihydroxy-9,13,18,18,20,20-hexamethyl-14-oxo-5,17,19-trioxapentacyclo[8.6.3.112,16.02,9.03,6]icos-12-en-3-yl] acetate
  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：

  13-乙酰基-9-羟基巴卡丁 III 、 2,2-二甲氧基丙烷 在 对甲苯磺酸 作用下， 以 丙酮 为溶剂， 反应 1.0h， 以90.4%的产率得到9(R)-dihydro-7,9-isopropylidene-13-acetylbaccatin-III
  参考文献：
  名称：

  加拿大红豆杉中主要紫杉烷的重排

  摘要：

  主要紫杉烷9-二氢-13-乙酰基浆果赤霉素III（重排1）至新的abeo- -taxanes（2,4-6）进行了研究。已经推断出一系列反应。它们的结构是通过光谱技术确定的。

  DOI：

  10.1016/0040-4039(96)01426-8

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。
• Acid catalyzed rearrangement and acyl migration studies on 9-dihydro-13-acetylbaccatin-III, a major taxane from Taxus canadensis
  作者：Lolita O. Zamir、Sarala Balachandran、Yi Feng Zheng、Maria E. Nedea、Gaétan Caron、Anastasia Nikolakakis、Ram A. Vishwakarma、Françoise Sauriol、Orval Mamer

  DOI：10.1016/s0040-4020(97)10069-2

  日期：1997.11

  A detailed investigation of the rearrangement of the major taxane from Taxus canadensis enables to suggest the sequence of the reactions involved: 9-dihydro- 13-acetylbaccatin III → abeo-taxanes with intact oxetane and acyl migration → abeo-taxanes with intact oxetane and deacylation → abeo-taxanes with opening of the oxetane and various acyl migrations including two unusual benzoyl shifts.

  从主要紫杉烷的重排的详细调查红豆杉飞蓬能够建议反应的序列涉及：9-二氢-13-乙酰基III→ ABEO -taxanes具有完整氧杂环丁烷和酰基转移→ ABEO -taxanes具有完整氧杂环丁烷和脱酰→ ABEO -taxanes与氧杂环丁烷的开和各种酰基迁移其中包括两个不同寻常的苯甲酰基的变化。
• 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.