10-deacetyl-9β-dihydrobaccatin III | 162475-68-5

• 英文名称: 10-deacetyl-9β-dihydrobaccatin III
• 英文别名: 9β-10-deacetyl-9-dihydrobaccatin III；10-deacetyl-9-β-hydroxybaccatin；[(1S,2S,3R,4S,7R,9S,10S,11S,12R,15S)-4-acetyloxy-1,9,11,12,15-pentahydroxy-10,14,17,17-tetramethyl-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate
• CAS: 162475-68-5
• 化学式: C₂₉H₃₈O₁₀
• 分子量: 546.615
• InChiKey: IEQWWEGDLRPQRW-XQPOBILRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  39
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  163
• 氢给体数：
  5
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  10-deacetyl-9β-dihydrobaccatin III 在 camphor-10-sulfonic acid 、 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 [(2R,6S,7S,8S,10R,13S,14R,15S,16S,18S)-13-acetyloxy-18-[(2R,3R)-3-(furan-2-yl)-3-[(2-methylpropan-2-yl)oxycarbonylamino]-2-tri(propan-2-yl)silyloxypropanoyl]oxy-8,16-dihydroxy-4,4,7,19,20,20-hexamethyl-3,5,11-trioxapentacyclo[14.3.1.02,6.07,14.010,13]icos-1(19)-en-15-yl] benzoate
  参考文献：
  名称：

  New highly active taxoids from 9β-Dihydrobaccatin-9,10-acetals

  摘要：

  To synthesize new highly active taxoids, we designed and synthesized 9beta-dihydro-9,10-acetal taxoids. In vitro study of these analogues clearly showed them to be more potent than docetaxel. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00069-0
• 作为产物：
  描述：

  10-脱乙酰基巴卡丁 III 在 tetrabutylammonium borohydride 作用下， 以 二氯甲烷 为溶剂， 生成 10-deacetyl-9β-dihydrobaccatin III
  参考文献：
  名称：

  C13 amido substituted taxane derivatives and pharmaceutical compositions containing them

  摘要：

  具有氨基取代的C13侧链的紫杉烷衍生物。

  公开号：

  US06369244B1

文献信息

• C2 substituted phenyl taxane derivatives and pharmaceutical compositions containing them
  申请人：Florida State University

  公开号：US06339164B1

  公开（公告）日：2002-01-15

  Taxane derivatives having alternative C2 substituents.

  具有替代C2取代基的紫杉烷衍生物。
• Taxane Compounds, Compositions And Methods
  申请人：Thottathil John K.

  公开号：US20120004429A1

  公开（公告）日：2012-01-05

  The present invention provides a method for the preparation of orally available pentacyclic taxane compounds, as well as intermediates useful in their preparation.

  本发明提供了一种制备口服五环紫杉烷类化合物的方法，以及在其制备中有用的中间体。
• TAXOL DERIVATIVES WITH ANTITUMOR ACTIVITY
  申请人：Shanghai Hengrui Pharmaceutical Co. Ltd.

  公开号：EP1980562A1

  公开（公告）日：2008-10-15

  Taxol derivatives or their salts having the formula as following: Wherein, R1, R2, Z1, Z2, Z3 and Z4 are defined as the description. Their preparation methods and their use as antitumor agent are also disclosed.

  紫杉醇衍生物或其盐的化学式如下：其中，R1、R2、Z1、Z2、Z3和Z4的定义如描述所示。还公开了它们的制备方法和作为抗肿瘤剂的用途。
• Stereoselective synthesis of 9β-hydroxytaxanes via reduction with samarium diiodide
  作者：Gunda I. Georg、Zacharia S. Cheruvallath、David G. Vander Velde、Richard H. Himes

  DOI：10.1016/0040-4039(95)00142-y

  日期：1995.3

  Reaction of baccatin III and paclitaxel with samarium diiodide yielded the corresponding l0-deacetyl-9 beta-hydroxy derivatives. When 10-deacetylbaccatin III and docetaxel were subjected to the same reaction conditions the corresponding 9 beta-hydroxy and 10-dehydroxy-9 beta-hydroxy analogues were isolated.
• The Chemistry of the Taxane Diterpene:  Stereoselective Reductions of Taxanes
  作者：Gunda I. Georg、Geraldine C. B. Harriman、Apurba Datta、Syed Ali、Zacharia Cheruvallath、Dinah Dutta、David G. Vander Velde、Richard H. Himes

  DOI：10.1021/jo981194s

  日期：1998.11.1

  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.