(4R,5S)-4-(Methoxycarbonyl)-5-<(4-phthalimido)butyl>oxazoline

• 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: (4R,5S)-4-(Methoxycarbonyl)-5-<(4-phthalimido)butyl>oxazoline
• 英文别名: methyl (4R,5S)-5-[3-(1,3-dioxoisoindol-2-yl)propyl]-4,5-dihydro-1,3-oxazole-4-carboxylate
• 化学式: C₁₆H₁₆N₂O₅
• 分子量: 316.313
• InChiKey: KQNCXOHURBDDRC-QWHCGFSZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  85.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4R,5S)-4-(Methoxycarbonyl)-5-<(4-phthalimido)butyl>oxazoline 在 盐酸 作用下， 反应 16.0h， 以76%的产率得到(-)-(2R,3S)-3-Hydroxylysine dihydrochloride
  参考文献：
  名称：

  Two Chiral Syntheses of threo-3-Hydroxylsine

  摘要：

  Two efficient chiral syntheses of 3-hydroxylysine, a naturally occurring amino acid and a putative intermediate in the synthesis of balanol, a potent protein kinase C inhibitor, are described. The synthesis of (2R,3S)-3-hydroxylysine utilizes Hayashi's chiral ferroceno gold catalyst. The synthesis of (2S,3R)-3-hydroxylysine demonstrates a beta-hydroxy amino acid synthesis with the chirality derived from the Sharpless chiral cis-hydroxylation.

  DOI：

  10.1021/jo00098a047
• 作为产物：
  描述：

  4-(1,3-二氧代异吲哚啉-2-基)丁醛 、 异腈基乙酸甲酯 在 bis(cyclohexylisocyanide)gold(I) tetrafluoroborate 、 (SR-BPPF-<(methylamino)ethyl>piperidine 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以90%的产率得到(4R,5S)-4-(Methoxycarbonyl)-5-<(4-phthalimido)butyl>oxazoline
  参考文献：
  名称：

  Two Chiral Syntheses of threo-3-Hydroxylsine

  摘要：

  Two efficient chiral syntheses of 3-hydroxylysine, a naturally occurring amino acid and a putative intermediate in the synthesis of balanol, a potent protein kinase C inhibitor, are described. The synthesis of (2R,3S)-3-hydroxylysine utilizes Hayashi's chiral ferroceno gold catalyst. The synthesis of (2S,3R)-3-hydroxylysine demonstrates a beta-hydroxy amino acid synthesis with the chirality derived from the Sharpless chiral cis-hydroxylation.

  DOI：

  10.1021/jo00098a047

文献信息

• Two Chiral Syntheses of threo-3-Hydroxylsine
  作者：Philip F. Hughes、Shelley H. Smith、John T. Olson

  DOI：10.1021/jo00098a047

  日期：1994.9

  Two efficient chiral syntheses of 3-hydroxylysine, a naturally occurring amino acid and a putative intermediate in the synthesis of balanol, a potent protein kinase C inhibitor, are described. The synthesis of (2R,3S)-3-hydroxylysine utilizes Hayashi's chiral ferroceno gold catalyst. The synthesis of (2S,3R)-3-hydroxylysine demonstrates a beta-hydroxy amino acid synthesis with the chirality derived from the Sharpless chiral cis-hydroxylation.