(2R,3S,5R)-3-hydroxy-2-hydroxymethyl-5-(trimethylsilylethynyl)tetrahydrofuran | 503057-22-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S,5R)-3-hydroxy-2-hydroxymethyl-5-(trimethylsilylethynyl)tetrahydrofuran
• 英文别名: (2R,3S,5R)-2-(hydroxymethyl)-5-(2-trimethylsilylethynyl)oxolan-3-ol
• CAS: 503057-22-5
• 化学式: C₁₀H₁₈O₃Si
• 分子量: 214.337
• InChiKey: VGRWGPWSWNQTDM-LPEHRKFASA-N

物化性质

• 熔点：
  64-65 °C
• 沸点：
  310.4±42.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.38
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4,4'-双甲氧基三苯甲基氯 、 (2R,3S,5R)-3-hydroxy-2-hydroxymethyl-5-(trimethylsilylethynyl)tetrahydrofuran 在 4-二甲氨基吡啶 作用下， 以 吡啶 为溶剂， 反应 1.0h， 以98%的产率得到(2R,3S,5R)-3-hydroxy-5-(trimethylsilylethynyl)-2-(4,4'-dimethoxytrityloxymethyl)tetrahydrofuran
  参考文献：
  名称：

  基于炔基C-核苷的人工DNA，可作为均聚物和异源受体的优良骨架。

  摘要：

  通过固相DNA合成，合成了由带有pyr，per和蒽作为荧光团的炔基β-D-呋喃核苷组成的DNA样荧光寡聚体。荧光低聚物具有确定数量和顺序的荧光团。在这些低聚物中，相邻的荧光团通过其电子基态中的疏水相互作用以面对面的方式彼此有效地相互作用。在含水介质中，不仅从均聚物（py-py和per-per体系）中观察到主要的准分子发射，而且还从杂聚物（（-per，-蒽和-蒽体系）中观察到。

  DOI：

  10.1002/chem.200700559
• 作为产物：
  描述：

  3,5-di-O-benzyl-2-deoxy-D-ribofuranose 在 正丁基锂 、 dicobalt octacarbonyl 、 三氯化硼 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 7.5h， 生成 (2R,3S,5R)-3-hydroxy-2-hydroxymethyl-5-(trimethylsilylethynyl)tetrahydrofuran
  参考文献：
  名称：

  Stereoselective Synthesis of Alkynyl C-2-Deoxy-β-d-ribofuranosides via Intramolecular Nicholas Reaction:  A Versatile Building Block for Nonnatural C-Nucleosides

  摘要：

  [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.

  DOI：

  10.1021/ol027210w

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.
• Artificial DNAs Based on AlkynylC-Nucleosides as a Superior Scaffold for Homo- and Heteroexcimer Emissions
  作者：Junya Chiba、Sakiko Takeshima、Kikyo Mishima、Hajime Maeda、Yasuaki Nanai、Kazuhiko Mizuno、Masahiko Inouye

  DOI：10.1002/chem.200700559

  日期：2007.10.5

  as a fluorophore were synthesized by solid-phase DNA synthesis. The fluorescent oligomers possess the defined number and order of the fluorophores. In these oligomers, the adjacent fluorophores efficiently interact with each other by hydrophobic interactions in their electronic ground states in a face-to-face fashion. The predominant excimer emissions were observed from not only the homooligomers (pyrene-pyrene

  通过固相DNA合成，合成了由带有pyr，per和蒽作为荧光团的炔基β-D-呋喃核苷组成的DNA样荧光寡聚体。荧光低聚物具有确定数量和顺序的荧光团。在这些低聚物中，相邻的荧光团通过其电子基态中的疏水相互作用以面对面的方式彼此有效地相互作用。在含水介质中，不仅从均聚物（py-py和per-per体系）中观察到主要的准分子发射，而且还从杂聚物（（-per，-蒽和-蒽体系）中观察到。