[(2S,3S,3aS,6R,6aR)-3-hydroxy-5-oxo-2-prop-2-ynoxy-3,3a,6,6a-tetrahydro-2H-furo[3,2-b]furan-6-yl] benzoate | 1285718-33-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2S,3S,3aS,6R,6aR)-3-hydroxy-5-oxo-2-prop-2-ynoxy-3,3a,6,6a-tetrahydro-2H-furo[3,2-b]furan-6-yl] benzoate
• CAS: 1285718-33-3
• 化学式: C₁₆H₁₄O₇
• 分子量: 318.283
• InChiKey: NIHUPFZWXUGISC-WKIHFJMMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  91.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [(2S,3S,3aS,6R,6aR)-3-hydroxy-5-oxo-2-prop-2-ynoxy-3,3a,6,6a-tetrahydro-2H-furo[3,2-b]furan-6-yl] benzoate 、 苄基叠氮 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 二氯甲烷 、 水 为溶剂， 以60%的产率得到[(2S,3S,3aS,6R,6aR)-2-[(1-benzyltriazol-4-yl)methoxy]-3-hydroxy-5-oxo-3,3a,6,6a-tetrahydro-2H-furo[3,2-b]furan-6-yl] benzoate
  参考文献：
  名称：

  Design and synthesis by click triazole formation of paclitaxel mimics with simplified core and side-chain structures

  摘要：

  A library of paclitaxel (taxol) mimics was obtained by a straightforward strategy involving rational design and an efficient synthesis of a simplified taxane core substitute, together with a click-chemistry combinatorial search for phenylisoserine side-chain surrogates. (c) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.01.081
• 作为产物：
  描述：

  、 2-丙炔-1-醇 在 硫酸 作用下， 反应 1.0h， 以69%的产率得到[(2S,3S,3aS,6R,6aR)-3-hydroxy-5-oxo-2-prop-2-ynoxy-3,3a,6,6a-tetrahydro-2H-furo[3,2-b]furan-6-yl] benzoate
  参考文献：
  名称：

  Design and synthesis by click triazole formation of paclitaxel mimics with simplified core and side-chain structures

  摘要：

  A library of paclitaxel (taxol) mimics was obtained by a straightforward strategy involving rational design and an efficient synthesis of a simplified taxane core substitute, together with a click-chemistry combinatorial search for phenylisoserine side-chain surrogates. (c) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.01.081

文献信息

• Design and synthesis by click triazole formation of paclitaxel mimics with simplified core and side-chain structures
  作者：Claire Le Manach、Aurélie Baron、Régis Guillot、Boris Vauzeilles、Jean-Marie Beau

  DOI：10.1016/j.tetlet.2011.01.081

  日期：2011.3

  A library of paclitaxel (taxol) mimics was obtained by a straightforward strategy involving rational design and an efficient synthesis of a simplified taxane core substitute, together with a click-chemistry combinatorial search for phenylisoserine side-chain surrogates. (c) 2011 Elsevier Ltd. All rights reserved.