(2R,3R)-2-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-piperidin-3-ol | 197244-39-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R)-2-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-piperidin-3-ol
• 英文别名: (2R,3R)-2-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]piperidin-3-ol
• CAS: 197244-39-6
• 化学式: C₁₀H₁₉NO₃
• 分子量: 201.266
• InChiKey: CLXOWBDHGYUDDY-HRDYMLBCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  50.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3R)-2-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-piperidin-3-ol 在 吡啶 、 4-二甲氨基吡啶 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 生成 Acetic acid (2S,3R)-1-acetyl-2-((R)-1,2-dihydroxy-ethyl)-piperidin-3-yl ester
  参考文献：
  名称：

  Total synthesis of both enentiomers of trans-β-hydroxyppecolic acid

  摘要：

  trans-beta-Hydroxypipecolic acids of both L-and D-series, L-1 and D-1, have been straightforwardly prepared in 14% and 15% yields, respectively starting from glyceraldehyde imines D-7 and L-7 as useful three-carbon chirons. The key feature of these parallel syntheses lies on the highly diastereoselective character of the initial coupling manoeuver between silyloxy furan TBSOF and imines 7, which ultimately accounts for the relative, and hence absolute configuration of the target pipecolic acids. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00344-3
• 作为产物：
  描述：

  (5R,6R)-6-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-5-hydroxy-piperidin-2-one 在 lithium aluminium tetrahydride 、 三氯化铝 作用下， 以 四氢呋喃 为溶剂， 反应 1.33h， 以74%的产率得到(2R,3R)-2-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-piperidin-3-ol
  参考文献：
  名称：

  Total synthesis of both enentiomers of trans-β-hydroxyppecolic acid

  摘要：

  trans-beta-Hydroxypipecolic acids of both L-and D-series, L-1 and D-1, have been straightforwardly prepared in 14% and 15% yields, respectively starting from glyceraldehyde imines D-7 and L-7 as useful three-carbon chirons. The key feature of these parallel syntheses lies on the highly diastereoselective character of the initial coupling manoeuver between silyloxy furan TBSOF and imines 7, which ultimately accounts for the relative, and hence absolute configuration of the target pipecolic acids. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00344-3