(4R,5S,6R,7R)-4-allylamino-5,6,7,8-tetrahydroxyoct-1-ene | 1361940-05-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4R,5S,6R,7R)-4-allylamino-5,6,7,8-tetrahydroxyoct-1-ene
• 英文别名: (2R,3R,4S,5R)-5-(prop-2-enylamino)oct-7-ene-1,2,3,4-tetrol
• CAS: 1361940-05-7
• 化学式: C₁₁H₂₁NO₄
• 分子量: 231.292
• InChiKey: BFEZJGGHXZWMSS-ZNSHCXBVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  16
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  93
• 氢给体数：
  5
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4R,5S,6R,7R)-4-allylamino-5,6,7,8-tetrahydroxyoct-1-ene 在 对甲苯磺酸 、 Hoveyda-Grubbs catalyst second generation 作用下， 以 二氯甲烷 为溶剂， 反应 16.5h， 以55%的产率得到(1S,2R,3R)-1-[(2R)-1,2,3,6-tetrahydropyridin-2-yl]butane-1,2,3,4-tetrol
  参考文献：
  名称：

  Highly Selective Indium Mediated Allylation of Unprotected Pentosylamines

  摘要：

  A straightforward functionalization of D-pentoses is reported, which affords homoallylaminopolyols in two steps and uses ion exchange chromatography as the only purification operation. The key indium-mediated allylation is effected on unprotected glycosylamines and occurs with good to excellent syn stereoselection. Validation of the synthetic utility of the method was exemplified by a 3-step synthesis of an optically active 1,2,3,6-tetrahydropyridine from D-xylose.

  DOI：

  10.1021/ol3002656
• 作为产物：
  描述：

  D-木糖 在 indium 作用下， 以 甲醇 为溶剂， 反应 0.17h， 生成 (4R,5S,6R,7R)-4-allylamino-5,6,7,8-tetrahydroxyoct-1-ene
  参考文献：
  名称：

  Highly Selective Indium Mediated Allylation of Unprotected Pentosylamines

  摘要：

  A straightforward functionalization of D-pentoses is reported, which affords homoallylaminopolyols in two steps and uses ion exchange chromatography as the only purification operation. The key indium-mediated allylation is effected on unprotected glycosylamines and occurs with good to excellent syn stereoselection. Validation of the synthetic utility of the method was exemplified by a 3-step synthesis of an optically active 1,2,3,6-tetrahydropyridine from D-xylose.

  DOI：

  10.1021/ol3002656

文献信息

• Highly Selective Indium Mediated Allylation of Unprotected Pentosylamines
  作者：Jean-Bernard Behr、Audrey Hottin、Alpha Ndoye

  DOI：10.1021/ol3002656

  日期：2012.3.16

  A straightforward functionalization of D-pentoses is reported, which affords homoallylaminopolyols in two steps and uses ion exchange chromatography as the only purification operation. The key indium-mediated allylation is effected on unprotected glycosylamines and occurs with good to excellent syn stereoselection. Validation of the synthetic utility of the method was exemplified by a 3-step synthesis of an optically active 1,2,3,6-tetrahydropyridine from D-xylose.