[(3aR,5R,6R,6aR)-5-[(1R)-2-[tert-butyl(dimethyl)silyl]oxy-1-hydroxyethyl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl] benzoate | 250696-85-6

• 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: [(3aR,5R,6R,6aR)-5-[(1R)-2-[tert-butyl(dimethyl)silyl]oxy-1-hydroxyethyl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl] benzoate
• CAS: 250696-85-6
• 化学式: C₂₂H₃₄O₇Si
• 分子量: 438.593
• InChiKey: BPVNCRFGMKNPLD-HGJKNBTDSA-N

物化性质

• 沸点：
  485.2±45.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.47
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [(3aR,5R,6R,6aR)-5-[(1R)-2-[tert-butyl(dimethyl)silyl]oxy-1-hydroxyethyl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl] benzoate 在 三乙基硅烷 、 18-冠醚-6 、 偶氮二异丁腈 、 三氟甲磺酸三甲基硅酯 、 四丁基氟化铵 、 三正丁基氢锡 、 sodium methylate 、 sodium hydride 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 28.0h， 生成 1-[(2R,3R)-2-(2-Benzyloxy-ethyl)-tetrahydro-furan-3-yl]-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Homologues of Isomeric Dideoxynucleosides as Potential Antiviral Agents: Synthesis of Isodideoxy-Nucleosides with a Furanethanol Sugar Moiety

  摘要：

  The synthesis of a homologues series of compounds related to (R, S)-isodideoxynucleosides has been completed by coupling a variety of natural purine and pyrimidine bases with a modified sugar intermediate. This sugar precursor was prepared regiospecifically and stereospecifically from D-glucose.

  DOI：

  10.1080/07328319908044857
• 作为产物：
  描述：

  1,2:5,6-二异亚丙基-alpha-D-异呋喃糖 在 咪唑 、 盐酸 作用下， 以 吡啶 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 14.0h， 生成 [(3aR,5R,6R,6aR)-5-[(1R)-2-[tert-butyl(dimethyl)silyl]oxy-1-hydroxyethyl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl] benzoate
  参考文献：
  名称：

  Homologues of Isomeric Dideoxynucleosides as Potential Antiviral Agents: Synthesis of Isodideoxy-Nucleosides with a Furanethanol Sugar Moiety

  摘要：

  The synthesis of a homologues series of compounds related to (R, S)-isodideoxynucleosides has been completed by coupling a variety of natural purine and pyrimidine bases with a modified sugar intermediate. This sugar precursor was prepared regiospecifically and stereospecifically from D-glucose.

  DOI：

  10.1080/07328319908044857

文献信息

• A Facile and Practical Synthesis of Peracylated 4-Thio-<scp>d</scp>-ribofuranoses from <scp>d</scp>-Glucose
  作者：Zhi-Hua Sun、Bing Wang

  DOI：10.1021/jo7026596

  日期：2008.3.1

  A practical synthesis of a peracylated 4-thio-D-ribofuranose 14 starting from inexpensive D-glucose is described. The C2-C6 portion Of D-glucose was utilized, in which sulfur was introduced to C5 in two consecutive displacement reactions with net retention of configuration under mild conditions.
• Homologues of Isomeric Dideoxynucleosides as Potential Antiviral Agents: Synthesis of Isodideoxy-Nucleosides with a Furanethanol Sugar Moiety
  作者：Xiaoping Zheng、Vasu Nair

  DOI：10.1080/07328319908044857

  日期：1999.9

  The synthesis of a homologues series of compounds related to (R, S)-isodideoxynucleosides has been completed by coupling a variety of natural purine and pyrimidine bases with a modified sugar intermediate. This sugar precursor was prepared regiospecifically and stereospecifically from D-glucose.