((1S,2S,4S,5R,6R)-5-acetamido-4-(tert-butoxycarbonylamino)-7-oxabicyclo[4.1.0]heptan-2-yl)dicyanomethyl acetate | 1171997-61-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ((1S,2S,4S,5R,6R)-5-acetamido-4-(tert-butoxycarbonylamino)-7-oxabicyclo[4.1.0]heptan-2-yl)dicyanomethyl acetate
• 英文别名: [[(1S,2S,4S,5R,6R)-5-acetamido-4-[(2-methylpropan-2-yl)oxycarbonylamino]-7-oxabicyclo[4.1.0]heptan-2-yl]-dicyanomethyl] acetate
• CAS: 1171997-61-7
• 化学式: C₁₈H₂₄N₄O₆
• 分子量: 392.412
• InChiKey: UOQUXKKKLOWCLY-SBJFKYEJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  154
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  ((1S,2S,4S,5R,6R)-5-acetamido-4-(tert-butoxycarbonylamino)-7-oxabicyclo[4.1.0]heptan-2-yl)dicyanomethyl acetate 在 bis(1,5-cyclooctadiene)nickel (0) 、 三丁基膦 作用下， 以 四氢呋喃 为溶剂， 以40%的产率得到
  参考文献：
  名称：

  An alternative synthesis of Tamiflu®: a synthetic challenge and the identification of a ruthenium-catalyzed dihydroxylation route

  摘要：

  Synthetic studies of Tamiflu (R) and the identification of a ruthenium-catalyzed dihydroxylation route are disclosed. This newly developed synthetic process circumvents the need for a Mitsunobu inversion step and the use of explosive reagents. This route, therefore, compares favorably to the previously developed synthetic process. (C) 2009 Elsevier Ltd. All rights reserved,

  DOI：

  10.1016/j.tet.2009.05.077
• 作为产物：
  描述：

  ((1S,4S,5S)-4-acetamido-5-(tert-butoxycarbonylamino)cyclohex-2-enyl)dicyanomethyl acetate 在 disodium hydrogenphosphate 、 双氧水 、 尿素 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 ((1S,2S,4S,5R,6R)-5-acetamido-4-(tert-butoxycarbonylamino)-7-oxabicyclo[4.1.0]heptan-2-yl)dicyanomethyl acetate
  参考文献：
  名称：

  钡催化不对称Diels-Alder型反应合成达菲

  摘要：

  为了寻求更好的途径：开发了新的达菲催化不对称合成方法。关键的转变是钡/ F 2 -FujiCAPO络合物在存在CsF助催化剂的情况下催化1和2的不对称Diels-Alder型反应，从而构成了达菲的核心（见方案； TMS =三甲基甲硅烷基）。以克为单位，将产品分11步转化为达菲。

  DOI：

  10.1002/anie.200804777

文献信息

• Design and Synthesis of Resin-Conjugated Tamiflu Analogs for Affinity Chromatography
  作者：Yasuaki Kimura、Kenzo Yamatsugu、Motomu Kanai、Noriko Echigo、Takashi Kuzuhara、Masakatsu Shibasaki

  DOI：10.5012/bkcs.2010.31.03.588

  日期：2010.3.20

  Two types of resin-conjugated Tamiflu analogs were synthesized by modifying our original synthetic route of oseltamivir phosphate (Tamiflu). The prepared resins bound to influenza virus neuraminidase, the main target of Tamiflu. The resins will be useful for isolating and identifying presumed endogenous vertebrate proteins that interact with Tamiflu, which might relate to the rarely observed abnormal behavior exhibited by some influenza patients treated with Tamiflu.

  通过修改磷酸奥司他韦（特敏福）的原始合成路线，我们合成了两种树脂结合的特敏福类似物。制备的树脂与流感病毒神经氨酸酶结合，而神经氨酸酶是达菲的主要靶标。这些树脂将有助于分离和鉴定与特敏福相互作用的假定内源性脊椎动物蛋白质，这可能与一些接受特敏福治疗的流感患者表现出的罕见异常行为有关。
• Design and synthesis of immobilized Tamiflu analog on resin for affinity chromatography
  作者：Yasuaki Kimura、Kenzo Yamatsugu、Motomu Kanai、Noriko Echigo、Takashi Kuzuhara、Masakatsu Shibasaki

  DOI：10.1016/j.tetlet.2009.01.142

  日期：2009.7

  A resin linked with the Tamiflu core was synthesized by modifying our original synthetic route Of oseltamivir phosphate (Tamiflu). The prepared resin bound to the influenza virus enzyme neuraminidase, the main target of Tamiflu. The immobilized Tamiflu analog will be useful for isolating and identifying presumed endogenous vertebrate proteins that interact with Tamiflu, which might relate to the abnormal behavior exhibited by some influenza patients treated with Tamiflu. (C) 2009 Elsevier Ltd. All rights reserved.