[(2S,3R)-2-azido-6-(1,3-dioxoisoindol-2-yl)-1-methoxy-1-oxohexan-3-yl] benzoate | 160146-93-0

• 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: [(2S,3R)-2-azido-6-(1,3-dioxoisoindol-2-yl)-1-methoxy-1-oxohexan-3-yl] benzoate
• CAS: 160146-93-0
• 化学式: C₂₂H₂₀N₄O₆
• 分子量: 436.424
• InChiKey: CXUVLUAJKAHKBE-MSOLQXFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  104
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  [(2S,3R)-2-azido-6-(1,3-dioxoisoindol-2-yl)-1-methoxy-1-oxohexan-3-yl] benzoate 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 反应 50.0h， 生成 (2S,3R)-3-hydroxylysine bis-hydrochloride
  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 在 N-溴代丁二酰亚胺(NBS) 、 sodium azide 、 K₂Os(OH)3 、 三氟化硼乙醚 、 potassium carbonate 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 、 potassium hexacyanoferrate(III) 作用下， 以 二氯甲烷 、 水 、 二甲基亚砜 、 叔丁醇 为溶剂， 反应 9.0h， 生成 [(2S,3R)-2-azido-6-(1,3-dioxoisoindol-2-yl)-1-methoxy-1-oxohexan-3-yl] benzoate
  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.