5,6-anhydro-3-O-benzoyl-1,2-O-isopropylidene-5-thio-α-D-gluco-pentofuranose | 1015447-32-1

• 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: 5,6-anhydro-3-O-benzoyl-1,2-O-isopropylidene-5-thio-α-D-gluco-pentofuranose
• 英文别名: [(3aR,5S,6S,6aR)-2,2-dimethyl-5-[(2S)-thiiran-2-yl]-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl] benzoate
• CAS: 1015447-32-1
• 化学式: C₁₆H₁₈O₅S
• 分子量: 322.382
• InChiKey: DVBBTEQUPYPGRK-FTQJZPFOSA-N

物化性质

• 沸点：
  436.4±45.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  79.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5,6-anhydro-3-O-benzoyl-1,2-O-isopropylidene-5-thio-α-D-gluco-pentofuranose 、 potassium acetate 、 乙酸酐 以 溶剂黄146 为溶剂， 反应 36.0h， 以92%的产率得到3-O-benzoyl-5,6-di-O,S-acetyl-1,2-O-isopropylidene-5-thio-α-D-gluco-pentofuranose
  参考文献：
  名称：

  A Facile and Practical Synthesis of Peracylated 4-Thio-d-ribofuranoses from d-Glucose

  摘要：

  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.

  DOI：

  10.1021/jo7026596
• 作为产物：
  描述：

  5,6-anhydro-3-O-benzoyl-1,2-O-isopropylidene-α-L-allo-pentofuranose 在 硫脲 作用下， 以 甲醇 为溶剂， 以73%的产率得到5,6-anhydro-3-O-benzoyl-1,2-O-isopropylidene-5-thio-α-D-gluco-pentofuranose
  参考文献：
  名称：

  A Facile and Practical Synthesis of Peracylated 4-Thio-d-ribofuranoses from d-Glucose

  摘要：

  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.

  DOI：

  10.1021/jo7026596