(3R,4S)-cis-4-(3-fluoro-pyridin-2-yl)-3-triisopropylsilyloxy-2-azetidinone | 457962-01-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: (3R,4S)-cis-4-(3-fluoro-pyridin-2-yl)-3-triisopropylsilyloxy-2-azetidinone
• 英文别名: (3R,4S)-4-(3-Fluoro-pyridin-2-yl)-3-triisopropylsilyloxy-2-azetidinone；(3R,4S)-4-(3-Fluoro-2-pyridyl)-3-triisopropylsilyloxy-2-azetidinone；(3R,4S)-4-(3-fluoropyridin-2-yl)-3-tri(propan-2-yl)silyloxyazetidin-2-one
• CAS: 457962-01-5
• 化学式: C₁₇H₂₇FN₂O₂Si
• 分子量: 338.497
• InChiKey: BQPANIBGEAPTOF-JKSUJKDBSA-N

物化性质

• 沸点：
  414.2±45.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.95
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  51.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3R,4S)-cis-4-(3-fluoro-pyridin-2-yl)-3-triisopropylsilyloxy-2-azetidinone 在 4-二甲氨基吡啶 、 potassium carbonate sodium hydride 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 异丙醚 为溶剂， 生成 (1S,2S,3R,4S,5R,8R,9S,10R,13S)-4-acetoxy-2-benzoyloxy-9,10-[(1S)-2-(dimethylamino)ethylidenedioxy]-5,20-epoxy-1-hydroxytax-11-en-13-yl (2R,3S)-3-(tert-butoxycarbonylamino)-3-(3-fluoro-2-pyridyl)-2-triisopropylsilyloxypropionate
  参考文献：
  名称：

  Taxane Compounds, Compositions And Methods

  摘要：

  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。

  公开号：

  US20120004429A1
• 作为产物：
  描述：

  3-氟吡啶-2-醛 在 咪唑 、 甲醇 、 ammonium cerium(IV) nitrate 、 potassium carbonate 、 sodium sulfate 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 、 苯 为溶剂， 生成 (3R,4S)-cis-4-(3-fluoro-pyridin-2-yl)-3-triisopropylsilyloxy-2-azetidinone
  参考文献：
  名称：

  New highly active taxoids from 9β-dihydrobaccatin-9,10-acetals. Part 5

  摘要：

  To improve the metabolic stability of 3, which exhibited both in vitro antitumor activity and in vivo efficacy by both iv and po administration, we designed and synthesized new taxane analogues. Most of the synthetic compounds maintained excellent antitumor activity and were scarcely metabolized by human liver microsomes. And some compounds exhibited potent antitumor effects against B16 melanoma BL6 in vivo by both iv and po administration similarly to 3. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.03.109

文献信息

• Pentacyclic taxan compound
  申请人：DAIICHI PHARMACEUTICAL CO., LTD.

  公开号：US20020143178A1

  公开（公告）日：2002-10-03

  This invention is to provide a novel taxol derivative useful as an antitumor compound having respective substituent groups, represented by the following formula (I) which can be orally administered. 1

  本发明提供了一种新型紫杉醇衍生物，具有相应的取代基团，可以口服使用，作为一种抗肿瘤化合物，其化学式如下：（I）
• METHOD FOR PRODUCING A 2-AZETIDINONE DERIVATIVE
  申请人：Daiichi Sankyo Company, Limited

  公开号：EP1375495B1

  公开（公告）日：2008-09-03
• New highly active taxoids from 9β-dihydrobaccatin-9,10-acetals. Part 5
  作者：Yasuyuki Takeda、Kouichi Uoto、Michio Iwahana、Takeshi Jimbo、Motoko Nagata、Ryo Atsumi、Chiho Ono、Noriko Tanaka、Hirofumi Terasawa、Tsunehiko Soga

  DOI：10.1016/j.bmcl.2004.03.109

  日期：2004.6

  To improve the metabolic stability of 3, which exhibited both in vitro antitumor activity and in vivo efficacy by both iv and po administration, we designed and synthesized new taxane analogues. Most of the synthetic compounds maintained excellent antitumor activity and were scarcely metabolized by human liver microsomes. And some compounds exhibited potent antitumor effects against B16 melanoma BL6 in vivo by both iv and po administration similarly to 3. (C) 2004 Elsevier Ltd. All rights reserved.
• 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。