(2R,3S,5S)-1,3-bis(benzyloxy)hept-6-yne-2,5-diol

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2R,3S,5S)-1,3-bis(benzyloxy)hept-6-yne-2,5-diol
• 英文别名: (2R,3S,5S)-1,3-bis(phenylmethoxy)hept-6-yne-2,5-diol
• 化学式: C₂₁H₂₄O₄
• 分子量: 340.419
• InChiKey: WNQGRDIOOJTSHR-NJYVYQBISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3S,5S)-1,3-bis(benzyloxy)hept-6-yne-2,5-diol 在 氢氧化钾 、 对甲苯磺酰氯 作用下， 以 水 、 丙酮 为溶剂， 反应 52.0h， 以65%的产率得到(2R,3S,5R)-3-benzyloxy-2-[(benzyloxy)methyl]-5-ethynyltetrahydrofuran
  参考文献：
  名称：

  Studies on the Generation of Unnatural C-Nucleosides with 1-Alkynyl-2-deoxy-d-riboses

  摘要：

  [GRAPHICS]1-Alkynyl-2-deoxy-D-riboses 7 and 8 were independently synthesized and subsequently used to generate several novel C-nucleosides.

  DOI：

  10.1021/ol701794u
• 作为产物：
  描述：

  2-deoxy-D-ribose 在 sodium hydride 、 乙酰氯 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 水 、 乙腈 、 mineral oil 为溶剂， 反应 50.0h， 生成 (2R,3S,5S)-1,3-bis(benzyloxy)hept-6-yne-2,5-diol 、 (2R,3S,5R)-1,3-bis(benzyloxy)hept-6-yne-2,5-diol
  参考文献：
  名称：

  通过Sonogashira偶联 有效合成荧光炔基C-核苷，用于制备基于DNA的多荧光团†

  摘要：

  提出了一种制备具有各种荧光团的炔基C-核苷的简便而通用的方法。Sonogashira偶联被用作关键反应，以使染料与易于获得的乙炔基官能化的脱氧核糖衍生物缀合。新的C-核苷用于制备基于DNA的多荧光团。

  DOI：

  10.1039/c6ob01199c

文献信息

• Stereoselective Synthesis of Alkynyl <i>C</i>-2-Deoxy-<i>β</i>-<scp>d</scp>-ribofuranosides via Intramolecular Nicholas Reaction:  A Versatile Building Block for Nonnatural <i>C</i>-Nucleosides
  作者：Masayoshi Takase、Tomoyuki Morikawa、Hajime Abe、Masahiko Inouye

  DOI：10.1021/ol027210w

  日期：2003.3.1

  [GRAPHICS]The reaction of 3,5-di-O-benzyl-2-deoxy-D-ribofuranose with various alkynyllithium reagents afforded diastereomeric mixtures of the corresponding ring-opened alkynyldiols. The resulting diastereomeric mixtures were successively treated with CO2(CO)(8), a catalytic amount of TfOH, Et3N, and iodine in one pot to give alkynyl C-3,5-di-O-benzyl-2-deoxy-beta-D-ribofuranosides with high beta-selectivities. The cobalt-mediated cyclization (intramolecular Nicholas reaction) is reversible; thus, thermodynamically more stable beta-anomers were obtained preferentially. The alkynyl C-deoxyribofuranosides were converted to a variety of C-deoxyribofuranoside derivatives.
• Studies on the Generation of Unnatural <i>C</i>-Nucleosides with 1-Alkynyl-2-deoxy-<scp>d</scp>-riboses
  作者：Mauro F. A. Adamo、Roberto Pergoli

  DOI：10.1021/ol701794u

  日期：2007.10.1

  [GRAPHICS]1-Alkynyl-2-deoxy-D-riboses 7 and 8 were independently synthesized and subsequently used to generate several novel C-nucleosides.
• Efficient synthesis of fluorescent alkynyl C-nucleosides via Sonogashira coupling for the preparation of DNA-based polyfluorophores
  作者：Dominik K. Kölmel、Luzi J. Barandun、Eric T. Kool

  DOI：10.1039/c6ob01199c

  日期：——

  A facile and general procedure for the preparation of alkynyl C-nucleosides with varied fluorophores is presented. Sonogashira coupling was used as a key reaction to conjugate the dyes to an easily accessible ethynyl functionalized deoxyribose derivative. The new C-nucleosides were used for the preparation of DNA-based polyfluorophores.

  提出了一种制备具有各种荧光团的炔基C-核苷的简便而通用的方法。Sonogashira偶联被用作关键反应，以使染料与易于获得的乙炔基官能化的脱氧核糖衍生物缀合。新的C-核苷用于制备基于DNA的多荧光团。