methyl 2,3,5-tri-O-benzoyl-α,β-4-thio-D-ribofuranoside | 1015447-25-2

• 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: methyl 2,3,5-tri-O-benzoyl-α,β-4-thio-D-ribofuranoside
• 英文别名: [(2R,3S,4R)-3,4-dibenzoyloxy-5-methoxythiolan-2-yl]methyl benzoate
• CAS: 1015447-25-2
• 化学式: C₂₇H₂₄O₇S
• 分子量: 492.549
• InChiKey: MECYIVJKFLNFAJ-IANNTBFTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  35
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  113
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 2,3,5-tri-O-benzoyl-α,β-4-thio-D-ribofuranoside 、 乙酸酐 在 硫酸 作用下， 以 溶剂黄146 为溶剂， 反应 1.0h， 以70%的产率得到2,3,5-tri-O-benzoyl-1-O-acetyl-β-4-thio-D-ribofuranose
  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：

  、 苯甲酰氯 以 吡啶 为溶剂， 以2.05 g的产率得到methyl 2,3,5-tri-O-benzoyl-α,β-4-thio-D-ribofuranoside
  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

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.