(3S,4R)-3-Triisopropylsilyloxy-4-phenylazetidin-2-one | 132201-31-1

• 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: (3S,4R)-3-Triisopropylsilyloxy-4-phenylazetidin-2-one
• 英文别名: (3S,4R)-4-phenyl-3-tri(propan-2-yl)silyloxyazetidin-2-one
• CAS: 132201-31-1
• 化学式: C₁₈H₂₉NO₂Si
• 分子量: 319.519
• InChiKey: UAXZZNDXCXGKHN-SJORKVTESA-N

物化性质

• 沸点：
  419.8±45.0 °C(Predicted)
• 密度：
  1.00±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.42
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3S,4R)-3-Triisopropylsilyloxy-4-phenylazetidin-2-one 在 吡啶 、 4-二甲氨基吡啶 、 氢氟酸 、 sodium hexamethyldisilazane 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 生成 2-debenzoyl-2-cinnamoyl-epi-paclitaxel
  参考文献：
  名称：

  Structure–activity relationship study of taxoids for their ability to activate murine macrophages as well as inhibit the growth of macrophage-like cells

  摘要：

  A series of new taxoids modified at the C-3', C-3'N, C-10, C-2 and C-7 positions has been designed, synthesized and evaluated for their potency to induce NO and TNF production by peritoneal murine macrophages (Mphi) from LPS-responsive C3H/HeN and LPS-hyporesponsive C3H/HeJ strains and human blood cells, and for their ability to inhibit the growth of Mphi-like cell lines J774.1 and J7.DEF3. The SAR-study has shown that the nature of the substituents at these positions have critical effect on the induction of TNF and NO production by Mphi. Positions G-3' and C-10 are the most flexible and an intriguing effect of the length of the substituents at the C-10 position is observed for taxoids bearing a straight chain alkanoyl moiety. An aromatic group at the C-3'N and C-2 positions is required for the activity, while only hydroxyl or acetyl substituents seem to be tolerated at the C-7 position. The natural stereochemistry in the C-13 isoserine side chain of the taxoids is an absolute requirement for macrophage activation. It has also been clearly shown that there is no correlation between the ability of the taxoids to induce TNF/NO production in C3H/HeN M and the cytotoxicity against Mphi-like cells. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00181-0
• 作为产物：
  描述：

  (+/-)-cis-3-acetoxy-1-(4-methoxyphenyl)-4-phenyl-2-azetidinone 在 lithium hydroxide 、 ammonium cerium(IV) nitrate 作用下， 以 水 、 丙酮 、 乙腈 为溶剂， 反应 8.0h， 生成 (3S,4R)-3-Triisopropylsilyloxy-4-phenylazetidin-2-one
  参考文献：
  名称：

  Synthesis of Docetaxel and Butitaxel Analogues through Kinetic Resolution of Racemic β-Lactams with 7-O-Triethylsilylbaccatin III

  摘要：

  The kinetic resolution of racemic cis-4-phenyl- and cis-4-tert-butyl-3-hydroxy-beta-lactam derivatives with 7-O-triethylsilylbaccatin III yielded paclitaxel and butitaxel analogues with high diastereoselectivity. The results demonstrated that the tert-butyldimethylsilyl protecting group at the C3-hydroxy group of the beta-lactams provided optimum kinetic resolution in comparison with the sterically less demanding triethylsilyl group and the larger triisopropylsilyl group. In addition, it was found that the C4 beta-lactam substituents also influenced diastereoselectivity. The C4 tert-butyl-beta-lactams provided better diastereoselectivity than the corresponding C4 phenyl beta-lactams.

  DOI：

  10.1021/jo061339s

文献信息

• New and efficient approaches to the semisynthesis of taxol and its C-13 side chain analogs by means of β-lactam synthon method
  作者：Iwao Ojima、Ivan Habus、Mangzhu Zhao、Martine Zucco、Young Hoon Park、Chung Ming Sun、Thierry Brigaud

  DOI：10.1016/s0040-4020(01)91210-4

  日期：1992.1

  Highly efficient chiral ester enolate-imine condensation giving 3-hydroxy-4-aryl-β-lactams with excellent enantiomeric purity is successfully applied to the asymmetric synthesis of the enantiomerically pure taxol C-13 side chain, N-benzoyl-(2R,3S)-3-phenyl-isoserine and its analogs. (3R,4S)-N-benzoyl-3-(1-ethoxyethoxy)-4-phenyl-2-azetidinone readily derived from the 3-hydroxy-4-phenyl-β-lactam is coupled

  高效手性酯烯酸酯-亚胺缩合可产生具有优异对映体纯度的3-羟基-4-芳基-β-内酰胺，已成功用于对映体纯紫杉醇C-13侧链N-苯甲酰基-（2 R， 3 S）-3-苯基-异丝氨酸及其类似物。易于衍生自3-羟基-4-苯基-β-内酰胺的（3 R，4 S）-N-苯甲酰基-3-（1-乙氧基乙氧基）-4-苯基-2-氮杂环丁酮与受保护的浆果赤霉素III偶联，然后通过脱保护得到光学纯的紫杉醇和高产率的10-脱乙酰基7,10-双（Troc）-紫杉醇。完全分配的1 H，13显示并讨论了由此合成的紫杉醇的C和2D（COSY和HETCOR）NMR光谱。
• Efficient and practical asymmetric synthesis of the taxol C-13 side chain, N-benzoyl-(2R,3S)-3-phenylisoserine, and its analogs via chiral 3-hydroxy-4-aryl-.beta.-lactams through chiral ester enolate-imine cyclocondensation
  作者：Iwao Ojima、Ivan Habus、Mangzhu Zhao、Gunda I. Georg、Lalith R. Jayasinghe

  DOI：10.1021/jo00005a003

  日期：1991.3

  A highly efficient chiral ester enolate-imine condensation giving 3-hydroxy-4-aryl-beta-lactams with > 96% ee is successfully applied to the asymmetric synthesis of the enantiomerically pure taxol C-13 side chain, N-benzoyl-(2R,3S)-3-phenylisoserine, and its analogues.
• Asymmetric Mannich-Type Addition of Lithium Glycolates to Imines Producing 3-Hydroxy-4-phenylazetidin-2-ones
  作者：Kiyoshi Tomioka、Hiroki Fujieda、Seiji Hata、Ken-ichi Yamada

  DOI：10.3987/com-05-s(k)40

  日期：——
• OJIMA, IWAO;HABUS, IVAN;ZHAO, MANGZHU;GEORG, GUNDA I.;JAYASINGHE, LALITH +, J. ORG. CHEM., 56,(1991) N, C. 1681-1683
  作者：OJIMA, IWAO、HABUS, IVAN、ZHAO, MANGZHU、GEORG, GUNDA I.、JAYASINGHE, LALITH +

  DOI：——

  日期：——