(2R,3S,5R)-3-Benzyloxy-2-benzyloxymethyl-5-prop-1-ynyl-tetrahydro-furan | 503057-29-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,3S,5R)-3-Benzyloxy-2-benzyloxymethyl-5-prop-1-ynyl-tetrahydro-furan
• CAS: 503057-29-2
• 化学式: C₂₂H₂₄O₃
• 分子量: 336.431
• InChiKey: WXJUWYIYSBMMAS-FDFHNCONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.97
• 重原子数：
  25.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  27.69
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (2R,3S,5R)-3-Benzyloxy-2-benzyloxymethyl-5-prop-1-ynyl-tetrahydro-furan 在 palladium dihydroxide 、 palladium on activated charcoal 4-二甲氨基吡啶 、 氢气 、 三乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 20.0 ℃ 、5.07 MPa 条件下， 反应 72.0h， 生成 4-Nitro-benzoic acid (2R,3S,5S)-2-(tert-butyl-diphenyl-silanyloxymethyl)-5-propyl-tetrahydro-furan-3-yl ester
  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：

  (2R,3S)-1,3-Bis-benzyloxy-hept-6-yne-2,5-diol 在 三氟甲磺酸 正丁基锂 、 dicobalt octacarbonyl 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 25.5h， 生成 (2R,3S,5R)-3-Benzyloxy-2-benzyloxymethyl-5-prop-1-ynyl-tetrahydro-furan
  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