6-O-tert-butyldimethylsilyl-5-(S)-acetyl-5-thio-3-O-benzoyl-1,2-O-isopropylidene-α-D-allofuranose | 1015447-24-1

• 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: 6-O-tert-butyldimethylsilyl-5-(S)-acetyl-5-thio-3-O-benzoyl-1,2-O-isopropylidene-α-D-allofuranose
• 英文别名: [(3aR,5S,6S,6aR)-5-[(1R)-1-acetylsulfanyl-2-[tert-butyl(dimethyl)silyl]oxyethyl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl] benzoate
• CAS: 1015447-24-1
• 化学式: C₂₄H₃₆O₇SSi
• 分子量: 496.697
• InChiKey: AFVMPVXNFPWEIF-CDVBAKLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.76
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  106
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  6-O-tert-butyldimethylsilyl-5-(S)-acetyl-5-thio-3-O-benzoyl-1,2-O-isopropylidene-α-D-allofuranose 在 三氟乙酸 作用下， 以 水 为溶剂， 反应 2.0h， 生成
  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：

  6-O-tert-butyldimethylsilyl-5-iodo-5-deoxy-3-O-benzoyl-1,2-O-isopropylidene-α-L-talofuranose 、 potassium thioacetate 以 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 以78%的产率得到6-O-tert-butyldimethylsilyl-5-(S)-acetyl-5-thio-3-O-benzoyl-1,2-O-isopropylidene-α-D-allofuranose
  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.