(5R,6S)-5-(dimethylamino)-4-(methoxymethoxy)-6-methyl-5,6-dihydropyran-2-one | 941674-07-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (5R,6S)-5-(dimethylamino)-4-(methoxymethoxy)-6-methyl-5,6-dihydropyran-2-one
• 英文别名: (2S,3R)-3-(dimethylamino)-4-(methoxymethoxy)-2-methyl-2,3-dihydropyran-6-one
• CAS: 941674-07-3
• 化学式: C₁₀H₁₇NO₄
• 分子量: 215.249
• InChiKey: RVEGOVVZDVRUIN-OIBJUYFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (5R,6S)-5-(dimethylamino)-4-(methoxymethoxy)-6-methyl-5,6-dihydropyran-2-one 在 palladium dihydroxide 氢气 作用下， 以 2,2,2-三氟乙醇 为溶剂， 反应 49.0h， 以82%的产率得到(4S,5R,6S)-5-(dimethylamino)-4-(methoxymethoxy)-6-methyl-tetrahydropyran-2-one
  参考文献：
  名称：

  Synthesis of l-Kedarosamine in Protected Form and Its Efficient Incorporation into an Advanced Intermediate to Kedarcidin Chromophore

  摘要：

  An efficient route to the complex L-kedarosamine alpha-glycosidic ether 2, a synthetic precursor to kedarcidin chromophore, is described. Central to the route, which is suitable for the preparation of multigram amounts of material, is a short synthetic sequence from D-threonine to protected L-kedarosamine derivatives and methodology for their alpha-selective coupling with appropriate hydroxyl acceptors.

  DOI：

  10.1021/ol070450x
• 作为产物：
  描述：

  (2R,3S)-methyl 3-hydroxy-2-(dimethylamino)butanoate 在 4-二甲氨基吡啶 、 三乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 (5R,6S)-5-(dimethylamino)-4-(methoxymethoxy)-6-methyl-5,6-dihydropyran-2-one
  参考文献：
  名称：

  Synthesis of l-Kedarosamine in Protected Form and Its Efficient Incorporation into an Advanced Intermediate to Kedarcidin Chromophore

  摘要：

  An efficient route to the complex L-kedarosamine alpha-glycosidic ether 2, a synthetic precursor to kedarcidin chromophore, is described. Central to the route, which is suitable for the preparation of multigram amounts of material, is a short synthetic sequence from D-threonine to protected L-kedarosamine derivatives and methodology for their alpha-selective coupling with appropriate hydroxyl acceptors.

  DOI：

  10.1021/ol070450x

文献信息

• Synthesis of <scp>l</scp>-Kedarosamine in Protected Form and Its Efficient Incorporation into an Advanced Intermediate to Kedarcidin Chromophore
  作者：Feng Ren、Philip C. Hogan、Alan J. Anderson、Andrew G. Myers

  DOI：10.1021/ol070450x

  日期：2007.5.1

  An efficient route to the complex L-kedarosamine alpha-glycosidic ether 2, a synthetic precursor to kedarcidin chromophore, is described. Central to the route, which is suitable for the preparation of multigram amounts of material, is a short synthetic sequence from D-threonine to protected L-kedarosamine derivatives and methodology for their alpha-selective coupling with appropriate hydroxyl acceptors.