7,13-diacetylbaccatin III | 92950-44-2

• 英文名称: 7,13-diacetylbaccatin III
• 英文别名: [(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,9,12,15-tetraacetyloxy-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate
• CAS: 92950-44-2
• 化学式: C₃₅H₄₂O₁₃
• 分子量: 670.711
• InChiKey: OLNLAMRZICZKJI-NIWDXWTNSA-N

物化性质

• 沸点：
  709.4±60.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  48
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  178
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  7,13-diacetylbaccatin III 在 红铝 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 以65%的产率得到7,13-O,O-diacetyl-2-O-debenzoylbaccatin III
  参考文献：
  名称：

  Point Mutations (Q19P and N23K) Increase the Operational Solubility of a 2α-O-Benzoyltransferase that Conveys Various Acyl Groups from CoA to a Taxane Acceptor

  摘要：

  Two site-directed Mutations within the wild-type 2-O-benzoyltransferase (tbt) cDNA, from Taxus cuspidata plants, yielded air encoded protein containing replacement amino acids at Q19P and N23K that trial) to a solvent-exposed loop region. The likely significant changes in the biophysical properties invoked by these mutations Caused the overexpressed, modified TBT (mTBT) to partition into the Soluble enzyme fraction about 5-fold greater than the wild-type enzyme. Sufficient protein could now be acquired to examine the scope of the substrate specificity of mTBT by incubation with 7,13-O,O-diacetyl-2-O-debenzoylbaceatin III that was mixed individually with various substituted benzoyls, alkanoyls, and (E)-butenoyl CoA donors. The mTBT catalyzed the conversion of each 7,13-O,O-diacetyl-2-O-debenzoylbaccatin III to several 7,13-O,O-diacetyl-2-O-acyl-2-O-debenzoylbaccatin III analogues. The relative catalytic efficiency of mTBT with the 7,13-O,O-diacetyl-2-O-debenzoyl surrogate Substrate and heterole carbonyl CoA substrates was slightly greater than with the natural aroyl substrate benzoyl CoA, While substituted benzoyl CoA thioesters were less productive. Short-chain hydrocarbon carbonyl and cyclohexanoyl CoA thioesters were also productive, where C-4 Substrates were transferred by mTBT with similar to 10- to 17-fold greater catalytic efficiency compared to the transfer of benzoyl. The described broad specificity of mTBT suggests (flat a plethora of 2-O-acyl variants of the antimitotic paclitaxel can be assembled through biocatalytic sequences.

  DOI：

  10.1021/np900524d
• 作为产物：
  描述：

  13-乙酰基-9-羟基巴卡丁 III 在 吡啶 、 chromium(VI) oxide 、 硫酸 作用下， 以 丙酮 为溶剂， 反应 19.0h， 生成 7,13-diacetylbaccatin III
  参考文献：
  名称：

  Taxus canadensis abundant taxane: conversion to paclitaxel and rearrangements

  摘要：

  An efficient conversion of Taxus canadensis abundant taxane, 9-dihydro-13-acetylbaccatin III to baccatin III is described. Since the synthesis of paclitaxel from baccatin III has been reported, this work can be used for additional supply of this powerful anticancer drug. In addition, new taxanes derived from skeletal rearrangements originating from oxidation-reduction reactions of the Canadian yew major taxane, are reported. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00056-0

文献信息

• [EN] SOLID STATE FORMS OF CABAZITAXEL AND PROCESSES FOR PREPARATION THEREOF<br/>[FR] FORMES SOLIDES DE CABAZITAXEL ET PROCÉDÉS DE PRÉPARATION ASSOCIÉS
  申请人：PLUS CHEMICALS SA

  公开号：WO2012142117A1

  公开（公告）日：2012-10-18

  The invention relates to solid state forms of Cabazitaxel, and processes for preparation, via novel synthetic intermediates, thereof, and formulations comprising one or more of the solid state forms of Cabazitaxel. The present invention further provides pharmaceutical compositions comprising one or more of the solid state forms of Cabazitaxel, and a method of treating hormone-refractory prostate cancer.

  本发明涉及卡巴地嗪的固态形式，以及制备它们的新型合成中间体的过程和包含一种或多种卡巴地嗪固态形式的制剂。本发明还提供了包含一种或多种卡巴地嗪固态形式的药物组合物，以及治疗激素难治性前列腺癌的方法。
• Chemical studies of 10-deacetyl baccatin III
  作者：F. Guéritte-Voegelein、V. Sénilh、B. David、D. Guénard、P. Potier

  DOI：10.1016/s0040-4020(01)87285-9

  日期：1986.1

  The chemical reactivities of 10-deacetyl baccatin III and of baccatin III, two natural products extracted from L., were studied with the aim of synthesizing taxol analogues having a modified side-chain at C-13, thereby restoring good binding to tubulin.

  为了合成在C-13具有侧链修饰的紫杉醇类似物，从而恢复与微管蛋白的良好结合，研究了从L.L.提取的两种天然产物10-脱乙酰基浆果赤霉素III和浆果赤霉素III的化学反应性。
• The chemistry of taxanes: reaction of taxol and baccatin derivatives with Lewis acids in aprotic and protic media
  作者：Shu-Hui Chen、Stella Huang、Jianmei Wei、Vittorio Farina

  DOI：10.1016/s0040-4020(01)80381-1

  日期：1993.4

  proceed via anchimeric assistance by the C-4 acetate group. Several minor products, including a novel derivative possessing a bridged C-ring, were also isolated. A mechanistic rationale is provided for all compounds formed. When taxol derivatives were treated with Lewis acids in methanol, ester cleavage reactions were observed. We provide conditions that are selective for C-10 acetate cleavage and

  几种路易斯酸被证明可以完全打开紫杉醇和浆果赤霉素衍生物的氧杂环丁烷环。已表明该反应是通过C-4乙酸酯基团通过邻氨基苯甲酸协助进行的。还分离了几种次要产物，包括具有桥C环的新型衍生物。提供了所形成的所有化合物的机械原理。当在甲醇中用路易斯酸处理紫杉醇衍生物时，观察到酯裂解反应。我们提供对C-10乙酸酯裂解和C-13侧链甲醇裂解具有选择性的条件。
• Reactivity of Baccatin III Derivatives towards Samarium II reagents
  作者：Sandrine Py、Françoise Khuong-Huu

  DOI：10.1016/0040-4039(95)00100-q

  日期：1995.3

  A study of the reactivity of 10-deacetylbaccatin III (1) towards samarium II reagents in the presence of various proton donors led to efficient synthesis of 9β-dihydro-10-deacetylbaccatin III (7) and 2-debenzoyl-9β-dihydro-10-deacetyl-baccatin III (9).

  在各种质子供体存在下10-去乙酰基浆果赤霉素III（1）对sa II试剂的反应性研究导致9β-二氢-10-去乙酰基浆果赤霉素III（7）和2-debenzoyl-9β-dihydro-10的有效合成。-脱乙酰基浆果赤霉素III（9）。
• Transacylases of the paclitaxel biosynthetic pathway
  申请人：Washington State University Research Foundation

  公开号：US07153676B1

  公开（公告）日：2006-12-26

  Transacylase enzymes and the use of such enzymes to produce paclitaxel, related taxoids, as well as intermediates in the paclitaxel biosynthetic pathway are disclosed. Also disclosed are nucleic acid sequences encoding the transacylase enzymes.

  本文揭示了转酰基酶酶和利用此类酶生产紫杉醇、相关紫杉烷类化合物以及紫杉醇生物合成途径中的中间体的方法。此外，还揭示了编码转酰基酶酶的核酸序列。