(5R,6R)-6-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-5-hydroxy-piperidin-2-one | 197244-38-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (5R,6R)-6-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-5-hydroxy-piperidin-2-one
• CAS: 197244-38-5
• 化学式: C₁₀H₁₇NO₄
• 分子量: 215.249
• InChiKey: AHPDQZKFECLYPE-BKPPORCPSA-N

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  (R)-5-[(R)-Amino-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-dihydro-furan-2-one 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 反应 4.0h， 以80%的产率得到(5R,6R)-6-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-5-hydroxy-piperidin-2-one
  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