[(2S,3S,4R,5S)-5-bromo-3,4-bis[(4-methylbenzoyl)oxy]oxolan-2-yl]methyl 4-methylbenzoate | 212499-71-3

• 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: [(2S,3S,4R,5S)-5-bromo-3,4-bis[(4-methylbenzoyl)oxy]oxolan-2-yl]methyl 4-methylbenzoate
• CAS: 212499-71-3
• 化学式: C₂₉H₂₇BrO₇
• 分子量: 567.433
• InChiKey: ONGYRGKJBDUJMT-QEGGNFSNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  37
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [(2S,3S,4R,5S)-5-bromo-3,4-bis[(4-methylbenzoyl)oxy]oxolan-2-yl]methyl 4-methylbenzoate 在 2,3,5-三甲基吡啶 、 盐酸 、 偶氮二异丁腈 、 三正丁基氢锡 、 溶剂黄146 作用下， 以 氘代氯仿 、 硝基甲烷 为溶剂， 反应 1.0h， 生成 1-氯-2-脱氧-3,5-二-O-对甲苯甲酰基-L-呋喃核糖
  参考文献：
  名称：

  Efficient Synthesis of 2-Deoxy l-Ribose from l-Arabinose:  Mechanistic Information on the 1,2-Acyloxy Shift in Alkyl Radicals

  摘要：

  [GRAPHICS]Conversion of the inexpensive L-arabinose 1 into the ethylthio ortho ester 7 followed by generation of the dialkoxyalkyl radical III produces the desired 2-deoxy-L-ribose triester 4 in excellent overall yield. It has been shown that the similar dialkoxyalkyl radical IV is not an intermediate in the 1,2-acyloxy shift of anomeric radical I.

  DOI：

  10.1021/ol990838v
• 作为产物：
  描述：

  (3R,4S,5S)-2-methoxy-4-((4-methylphenyl)carbonyloxy)-5-(((4-methylphenyl)carbonyloxy)methyl)oxolan-3-yl 4-methylbenzoate 在 氢溴酸 、 溶剂黄146 作用下， 生成 [(2S,3S,4R,5S)-5-bromo-3,4-bis[(4-methylbenzoyl)oxy]oxolan-2-yl]methyl 4-methylbenzoate
  参考文献：
  名称：

  Efficient Synthesis of 2-Deoxy l-Ribose from l-Arabinose:  Mechanistic Information on the 1,2-Acyloxy Shift in Alkyl Radicals

  摘要：

  [GRAPHICS]Conversion of the inexpensive L-arabinose 1 into the ethylthio ortho ester 7 followed by generation of the dialkoxyalkyl radical III produces the desired 2-deoxy-L-ribose triester 4 in excellent overall yield. It has been shown that the similar dialkoxyalkyl radical IV is not an intermediate in the 1,2-acyloxy shift of anomeric radical I.

  DOI：

  10.1021/ol990838v

文献信息

• Efficient Synthesis of 2-Deoxy <scp>l</scp>-Ribose from <scp>l</scp>-Arabinose:  Mechanistic Information on the 1,2-Acyloxy Shift in Alkyl Radicals
  作者：Michael E. Jung、Yue Xu

  DOI：10.1021/ol990838v

  日期：1999.11.1

  [GRAPHICS]Conversion of the inexpensive L-arabinose 1 into the ethylthio ortho ester 7 followed by generation of the dialkoxyalkyl radical III produces the desired 2-deoxy-L-ribose triester 4 in excellent overall yield. It has been shown that the similar dialkoxyalkyl radical IV is not an intermediate in the 1,2-acyloxy shift of anomeric radical I.