(4R,5S)-4,5-Bis-benzyloxy-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-morpholin-4-yl-2-p-tolyl-pentanenitrile | 436148-67-3

• 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: (4R,5S)-4,5-Bis-benzyloxy-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-morpholin-4-yl-2-p-tolyl-pentanenitrile
• CAS: 436148-67-3
• 化学式: C₃₅H₄₂N₂O₅
• 分子量: 570.729
• InChiKey: RQHDFHJVNCWYDW-NKYDFPKTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.76
• 重原子数：
  42.0
• 可旋转键数：
  12.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  73.18
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (4R,5S)-4,5-Bis-benzyloxy-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-morpholin-4-yl-2-p-tolyl-pentanenitrile 在 硫酸 、 水 、 copper(II) sulfate 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 12.5h， 生成 2-((2S,3R,4R)-3-Benzyloxy-4-hydroxy-tetrahydro-furan-2-yl)-1-p-tolyl-ethanone
  参考文献：
  名称：

  Umpolung Strategy for the Synthesis of 2-Deoxy-C-aryl Glycosides:  A Serendipitous, Efficient Route for C-Furanoside Analogues

  摘要：

  [GRAPHICS]2-Deoxy-C-aryl glycosides are potential synthetic targets as they form a very vital moiety of several biologically active natural products. This paper describes a synthetic route using an umpolung strategy, which has not been explored till date. Our synthetic endeavor led to a versatile intermediate aryl ketone 10, which has paved the way for two important classes of C-glycosides, viz, C-alkyl furanosides 12 and methyl 2-deoxy-C-aryl pyranosides 14.

  DOI：

  10.1021/ol025794w
• 作为产物：
  描述：

  2,3-di-O-benzyl-4,5-O-isopropylidene-D-arabinitol 在 4-二甲氨基吡啶 、 sodium hydride 、 碳酸氢钠 、 三乙胺 、 sodium iodide 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 25.0h， 生成 (4R,5S)-4,5-Bis-benzyloxy-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-morpholin-4-yl-2-p-tolyl-pentanenitrile
  参考文献：
  名称：

  Umpolung Strategy for the Synthesis of 2-Deoxy-C-aryl Glycosides:  A Serendipitous, Efficient Route for C-Furanoside Analogues

  摘要：

  [GRAPHICS]2-Deoxy-C-aryl glycosides are potential synthetic targets as they form a very vital moiety of several biologically active natural products. This paper describes a synthetic route using an umpolung strategy, which has not been explored till date. Our synthetic endeavor led to a versatile intermediate aryl ketone 10, which has paved the way for two important classes of C-glycosides, viz, C-alkyl furanosides 12 and methyl 2-deoxy-C-aryl pyranosides 14.

  DOI：

  10.1021/ol025794w