(S)-2-[(9H-fluoren-9-yl)methoxycarbonylamino]-3-hydroxy-N-methoxy-N-methylpropionamide | 684270-35-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (S)-2-[(9H-fluoren-9-yl)methoxycarbonylamino]-3-hydroxy-N-methoxy-N-methylpropionamide
• 英文别名: (9H-fluoren-9-yl)methyl (S)-(3-hydroxy-1-(methoxy(methyl)amino)-1-oxopropan-2-yl)carbamate；9H-fluoren-9-ylmethyl N-[(2S)-3-hydroxy-1-[methoxy(methyl)amino]-1-oxopropan-2-yl]carbamate
• CAS: 684270-35-7
• 化学式: C₂₀H₂₂N₂O₅
• 分子量: 370.405
• InChiKey: UKFOZAHCVHYBEV-SFHVURJKSA-N

物化性质

• 密度：
  1.280±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  88.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-2-[(9H-fluoren-9-yl)methoxycarbonylamino]-3-hydroxy-N-methoxy-N-methylpropionamide 在 lithium hydroxide 、 双氧水 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 16.08h， 生成 (S)-3-叠氮基-2-(Fmoc-氨基)丙酸 Fmoc-3-叠氮基-L-丙氨酸
  参考文献：
  名称：

  A Short Synthetic Approach to Chiral Serine Azido Derivatives

  摘要：

  我们报道了一种新的合成方法，通过将N保护的（Boc、Cbz和Fmoc）丝氨酸氨基酸转化为相应的Weinreb酰胺，合成手性丝氨酸叠氮衍生物。因此，丝氨酸的α-质子的酸性降低，这允许在Weinreb酰胺上进行亲核加成反应，从而生成手性丝氨酸叠氮衍生物。

  DOI：

  10.1055/s-2004-817770
• 作为产物：
  描述：

  二甲羟胺盐酸盐 、 Fmoc-L-丝氨酸 在 1-丙基磷酸酐 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 乙酸乙酯 、 乙腈 为溶剂， 反应 0.67h， 以89%的产率得到(S)-2-[(9H-fluoren-9-yl)methoxycarbonylamino]-3-hydroxy-N-methoxy-N-methylpropionamide
  参考文献：
  名称：

  Efficient synthesis of N-protected amino/peptide Weinreb amides from T3P and DBU

  摘要：

  The reaction of N-alpha-protected amino/peptide acid with N,O-dimethylhydroxylamine hydrochloride in the presence of T3P and DBU to obtain enantiomerically pure N-alpha-protected amino/peptidyl Weinreb amides in high yields has been described. Fmoc-Ala-Weinreb amide 2a is obtained as single crystal, and its structure was determined through X-ray crystallography. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.11.064

文献信息

• Direct Synthesis of N-Protected Serine- and Threonine-Derived Weinreb Amides via Diboronic Acid Anhydride-Catalyzed Dehydrative Amidation: Application to the Concise Synthesis of ­Garner’s Aldehyde
  作者：Naoyuki Shimada、Naoki Ohse、Naoya Takahashi、Sari Urata、Masayoshi Koshizuka、Kazuishi Makino

  DOI：10.1055/s-0037-1610773

  日期：2021.6

  for the direct synthesis of Weinreb amides derived from serine and threonine derivatives via diboronic acid anhydride-catalyzed hydroxy-directed amidation is described. This is the first successful example of the synthesis of serine- or threonine-derived Weinreb amides using catalytic dehydrative amidations. The methodology could be applied to the concise synthesis of Garner’s aldehyde.

  描述了一种有效的方法，该方法通过二硼酸酐催化的羟基定向酰胺化直接合成衍生自丝氨酸和苏氨酸衍生物的Weinreb酰胺。这是使用催化脱水酰胺化合成丝氨酸或苏氨酸衍生的Weinreb酰胺的第一个成功实例。该方法可用于加纳醛的简明合成。
• Solid-phase synthesis of a combinatorial library of dihydroceramide analogues and its activity in human alveolar epithelial cells
  作者：Gemma Villorbina、Daniel Canals、Lydia Carde、Santiago Grijalvo、Rosalia Pascual、Obdulia Rabal、Jordi Teixidó、Gemma Fabriàs、Amadeu Llebaria、Josefina Casas

  DOI：10.1016/j.bmc.2006.10.024

  日期：2007.1.1

  Solid-phase synthesis of a small combinatorial library of dihydroceramide analogues as mixtures of erythro and threo diastereomers is described. Some dihydroceramide analogues cause growth arrest and apoptosis in a dose-dependent manner in human alveolar epithelial cells. This activity is likely due to the threo isomers, as evidenced by cellular studies with a pair of diastereomerically pure N-acyldihydrosphingosines. The apoptotic activity reported in this work provides information for the design of new compounds that may provide the basis for the generation of biochemical tools for the study of different pathologies where ceramide and/or dihydroceramide are involved. (c) 2006 Elsevier Ltd. All rights reserved.