(1'E,4S,5R)-cis-3-benzyl-4-hydroxymethyl-5-(pentadec-1-enyl)-1,3-oxazolidin-2-one | 871259-43-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (1'E,4S,5R)-cis-3-benzyl-4-hydroxymethyl-5-(pentadec-1-enyl)-1,3-oxazolidin-2-one
• 英文别名: (4S,5R)-3-benzyl-4-(hydroxymethyl)-5-[(E)-pentadec-1-enyl]-1,3-oxazolidin-2-one
• CAS: 871259-43-7
• 化学式: C₂₆H₄₁NO₃
• 分子量: 415.616
• InChiKey: ANVBRBKZZNCYJC-PNIUMYDHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  30
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1'E,4S,5R)-cis-3-benzyl-4-hydroxymethyl-5-(pentadec-1-enyl)-1,3-oxazolidin-2-one 在 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 2.08h， 生成 [4S-[4α,5α(E)]]-4-(hydroxymethyl)-5-(1-pentadecenyl)-2-oxazolidinone
  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 、 锂硼氢 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 60.5h， 生成 (1'E,4S,5R)-cis-3-benzyl-4-hydroxymethyl-5-(pentadec-1-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

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.