(3R,4S)-2-Oxo-4-phenyl-3-triethylsilanyloxy-azetidine-1-carboxylic acid isopropyl ester | 393547-86-9

• 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)-2-Oxo-4-phenyl-3-triethylsilanyloxy-azetidine-1-carboxylic acid isopropyl ester
• 英文别名: propan-2-yl (3R,4S)-2-oxo-4-phenyl-3-triethylsilyloxyazetidine-1-carboxylate
• CAS: 393547-86-9
• 化学式: C₁₉H₂₉NO₄Si
• 分子量: 363.529
• InChiKey: VIKLBYMZWAHRRV-DLBZAZTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.51
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3R,4S)-2-Oxo-4-phenyl-3-triethylsilanyloxy-azetidine-1-carboxylic acid isopropyl ester 在 triethylamine trihydrofluoride 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 2.17h， 生成 4-O-deacetyl-3'-N-debenzoyl-3'-N-isopropoxycarbonyl-4-O-methoxycarbonylpaclitaxel
  参考文献：
  名称：

  The discovery of BMS-275183: an orally efficacious novel taxane

  摘要：

  The evolution of 2, a C-4-methylcarbonate analogue of paclitaxel with minimal oral bioavailability and oral efficacy, into its C-3'-t-butyl-3'-N-t-butyloxycarbonyl analogue (15i), a novel taxane with oral efficacy in preclinical models that is comparable to iv administered paclitaxel, is described. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00495-4
• 作为产物：
  描述：

  氯甲酸异丙酯 、 (3R,4S)-4-苯基-3-[(三乙基硅烷基)氧基]-2-氮杂环丁酮 在 4-二甲氨基吡啶 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 (3R,4S)-2-Oxo-4-phenyl-3-triethylsilanyloxy-azetidine-1-carboxylic acid isopropyl ester
  参考文献：
  名称：

  The discovery of BMS-275183: an orally efficacious novel taxane

  摘要：

  The evolution of 2, a C-4-methylcarbonate analogue of paclitaxel with minimal oral bioavailability and oral efficacy, into its C-3'-t-butyl-3'-N-t-butyloxycarbonyl analogue (15i), a novel taxane with oral efficacy in preclinical models that is comparable to iv administered paclitaxel, is described. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00495-4

文献信息

• Synthesis and Antitumor Activity of Novel C-7 Paclitaxel Ethers:  Discovery of BMS-184476
  作者：Thomas J. Altstadt、Craig R. Fairchild、Jerzy Golik、Kathy A. Johnston、John F. Kadow、Francis Y. Lee、Byron H. Long、William C. Rose、Dolatrai M. Vyas、Henry Wong、Mu-Jen Wu、Mark D. Wittman

  DOI：10.1021/jm0102607

  日期：2001.12.1

  The preparation of C-7 paclitaxel ethers is described. Various substituted ethers were prepared via activation of the corresponding methylthiomethyl ether followed by alcohol addition. Variation of the C-7 ether group as well the 3' side chain position led to the discovery of a novel taxane, BMS-184476 (4), with preclinical antitumor activity superior to paclitaxel.
• The discovery of BMS-275183: an orally efficacious novel taxane
  作者：Harold Mastalerz、Donald Cook、Craig R Fairchild、Steven Hansel、Walter Johnson、John F Kadow、Byron H Long、William C Rose、James Tarrant、Mu-Jen Wu、May Quifen Xue、Guifen Zhang、Mary Zoeckler、Dolatrai M Vyas

  DOI：10.1016/s0968-0896(03)00495-4

  日期：2003.10

  The evolution of 2, a C-4-methylcarbonate analogue of paclitaxel with minimal oral bioavailability and oral efficacy, into its C-3'-t-butyl-3'-N-t-butyloxycarbonyl analogue (15i), a novel taxane with oral efficacy in preclinical models that is comparable to iv administered paclitaxel, is described. (C) 2003 Elsevier Ltd. All rights reserved.