(2R,3S,5R)-3-benzyloxy-2-benzyloxymethyl-5-(trimethylsilylethynyl)tetrahydrofuran | 503057-02-1

• 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-benzyloxy-2-benzyloxymethyl-5-(trimethylsilylethynyl)tetrahydrofuran
• 英文别名: trimethyl-[2-[(2R,4S,5R)-4-phenylmethoxy-5-(phenylmethoxymethyl)oxolan-2-yl]ethynyl]silane
• CAS: 503057-02-1
• 化学式: C₂₄H₃₀O₃Si
• 分子量: 394.586
• InChiKey: XGMJAXSNKYSEAZ-KMDXXIMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.83
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,3S,5R)-3-benzyloxy-2-benzyloxymethyl-5-(trimethylsilylethynyl)tetrahydrofuran 在 三氯化硼 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以93%的产率得到(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
• 作为产物：
  描述：

  3,5-di-O-benzyl-2-deoxy-D-ribofuranose 在 吡啶 、 正丁基锂 、 对甲苯磺酰氯 作用下， 以 四氢呋喃 、 正己烷 、 氯仿 为溶剂， 反应 12.0h， 生成 (2R,3S,5R)-3-benzyloxy-2-benzyloxymethyl-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.