t-butyl (2R,3R,4E)-2-benzylamino-3-hydroxyoctadec-4-enoate | 871259-30-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: t-butyl (2R,3R,4E)-2-benzylamino-3-hydroxyoctadec-4-enoate
• 英文别名: tert-butyl (E,2R,3R)-2-(benzylamino)-3-hydroxyoctadec-4-enoate
• CAS: 871259-30-2
• 化学式: C₂₉H₄₉NO₃
• 分子量: 459.713
• InChiKey: XPPMMKNYQRSILJ-XONXXHEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  33
• 可旋转键数：
  20
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  t-butyl (2R,3R,4E)-2-benzylamino-3-hydroxyoctadec-4-enoate 在 lithium aluminium tetrahydride 、 四丁基氟化铵 、 氨 、 lithium 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 14.25h， 生成 (2'E,4S,1'R)-4-(1'-hydroxyhexadec-2'-enyl)-1,3-oxazolidin-2-one
  参考文献：
  名称：

  Chirality Transfer from Guanidinium Ylides to 3-Alkenyl (or 3-Alkynyl) Aziridine-2-carboxylates and Application to the Syntheses of (2R,3S)-3-Hydroxyleucinate and d-erythro-Sphingosine

  摘要：

  Reaction of chiral guanidinium ylides with alpha,beta-unsaturated aldehydes gives 3-(alpha,beta-unsaturated) aziridine-2-carboxylates in high diastereo- and enantioselectivities (up to 93% diastereomeric excess and 98% enantiomeric excess). 3-(l-Methylvinyl)- and 3-[(E)-pentadec-1-enyllaziridine-2-carboxylates were successfully employed to prepare (2R,3S)-3-hydroxyleucinate and D-erythro-sphingosine, respectively.

  DOI：

  10.1021/jo051495j
• 作为产物：
  描述：

  t-butyl (2R,3R,4E)-2-benzylamino-3-acetoxyoctadec-4-enoate 在 氢氧化钾 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.25h， 以99%的产率得到t-butyl (2R,3R,4E)-2-benzylamino-3-hydroxyoctadec-4-enoate
  参考文献：
  名称：

  Chirality Transfer from Guanidinium Ylides to 3-Alkenyl (or 3-Alkynyl) Aziridine-2-carboxylates and Application to the Syntheses of (2R,3S)-3-Hydroxyleucinate and d-erythro-Sphingosine

  摘要：

  Reaction of chiral guanidinium ylides with alpha,beta-unsaturated aldehydes gives 3-(alpha,beta-unsaturated) aziridine-2-carboxylates in high diastereo- and enantioselectivities (up to 93% diastereomeric excess and 98% enantiomeric excess). 3-(l-Methylvinyl)- and 3-[(E)-pentadec-1-enyllaziridine-2-carboxylates were successfully employed to prepare (2R,3S)-3-hydroxyleucinate and D-erythro-sphingosine, respectively.

  DOI：

  10.1021/jo051495j

文献信息

• Chirality Transfer from Guanidinium Ylides to 3-Alkenyl (or 3-Alkynyl) Aziridine-2-carboxylates and Application to the Syntheses of (2<i>R</i>,3<i>S</i>)-3-Hydroxyleucinate and <scp>d</scp>-<i>e</i><i>rythro</i>-Sphingosine
  作者：Wannaporn Disadee、Tsutomu Ishikawa

  DOI：10.1021/jo051495j

  日期：2005.11.1

  Reaction of chiral guanidinium ylides with alpha,beta-unsaturated aldehydes gives 3-(alpha,beta-unsaturated) aziridine-2-carboxylates in high diastereo- and enantioselectivities (up to 93% diastereomeric excess and 98% enantiomeric excess). 3-(l-Methylvinyl)- and 3-[(E)-pentadec-1-enyllaziridine-2-carboxylates were successfully employed to prepare (2R,3S)-3-hydroxyleucinate and D-erythro-sphingosine, respectively.