(2R,3S,5S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-propyl-tetrahydro-furan-3-ol | 503057-33-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S,5S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-propyl-tetrahydro-furan-3-ol
• CAS: 503057-33-8
• 化学式: C₂₄H₃₄O₃Si
• 分子量: 398.618
• InChiKey: FGASVEROJTWHGR-AJSBUHFISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.88
• 重原子数：
  28.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  38.69
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (2R,3S,5S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-propyl-tetrahydro-furan-3-ol 、 4-硝基苯甲酰氯 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以37%的产率得到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,5R)-3-benzyloxy-2-[(benzyloxy)methyl]-5-ethynyltetrahydrofuran 在 palladium dihydroxide 、 palladium on activated charcoal 4-二甲氨基吡啶 、 正丁基锂 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 乙酸乙酯 为溶剂， 20.0 ℃ 、5.07 MPa 条件下， 反应 66.5h， 生成 (2R,3S,5S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-propyl-tetrahydro-furan-3-ol
  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