(4R,5S,4'S,5'S)-5'-Bromomethyl-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-carbaldehyde O-benzyl-oxime | 140390-42-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4R,5S,4'S,5'S)-5'-Bromomethyl-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-carbaldehyde O-benzyl-oxime
• CAS: 140390-42-7；140390-43-8
• 化学式: C₁₉H₂₆BrNO₅
• 分子量: 428.323
• InChiKey: URUFXSOEWUSVJB-YYIAUSFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.62
• 重原子数：
  26.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  58.51
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (4R,5S,4'S,5'S)-5'-Bromomethyl-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-carbaldehyde O-benzyl-oxime 在 palladium on activated charcoal 偶氮二异丁腈 、 氢气 、 三正丁基氢锡 、 溶剂黄146 作用下， 以 甲醇 、 水 、 甲苯 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 43.0h， 生成 1-deamino-2-deoxy-1-epi-hydroxystreptamine
  参考文献：
  名称：

  6-Exo free radical cyclization of acyclic carbohydrate intermediates: a new synthetic route to enantiomerically pure polyhydroxylated cyclohexane derivatives

  摘要：

  The 6-exo free radical cyclization of conveniently functionalized acyclic carbohydrate derivatives is a new and efficient method for the asymmetric synthesis of polyhydroxylated cyclohexane compounds (aminocyclitols, pseudosugars). The scope and versatility of this synthetic route has been analyzed by changing the absolute configuration of the radical precursors and the nature of the radical trap. The yield and stereoselectivity in this process is very structure dependent.

  DOI：

  10.1021/jo00035a017
• 作为产物：
  描述：

  (4S,5R,4'S,5'S)-5-(Bis-ethylsulfanyl-methyl)-5'-bromomethyl-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl] 在 吡啶 、 mercury(II) oxide 、 mercury(II) chloride 作用下， 以 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 18.0h， 生成 (4R,5S,4'S,5'S)-5'-Bromomethyl-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-carbaldehyde O-benzyl-oxime
  参考文献：
  名称：

  6-Exo free radical cyclization of acyclic carbohydrate intermediates: a new synthetic route to enantiomerically pure polyhydroxylated cyclohexane derivatives

  摘要：

  The 6-exo free radical cyclization of conveniently functionalized acyclic carbohydrate derivatives is a new and efficient method for the asymmetric synthesis of polyhydroxylated cyclohexane compounds (aminocyclitols, pseudosugars). The scope and versatility of this synthetic route has been analyzed by changing the absolute configuration of the radical precursors and the nature of the radical trap. The yield and stereoselectivity in this process is very structure dependent.

  DOI：

  10.1021/jo00035a017