tert-butyl (2S,3R,4E)-1-hydroxy-3-(methoxymethoxy)octadec-4-en-2-yl-carbamate | 246245-47-6

• 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: tert-butyl (2S,3R,4E)-1-hydroxy-3-(methoxymethoxy)octadec-4-en-2-yl-carbamate
• 英文别名: tert-butyl (2S,3R,E)-1-hydroxy-3-(methoxymethoxy)octadec-4-en-2-ylcarbamate；tert-butyl-(2S,3R,4E)-1-hydroxy-3-(methoxymethoxy)octadec-4-en-2-yl-carbamate；tert-butyl N-[(E,2S,3R)-1-hydroxy-3-(methoxymethoxy)octadec-4-en-2-yl]carbamate
• CAS: 246245-47-6
• 化学式: C₂₅H₄₉NO₅
• 分子量: 443.668
• InChiKey: FEESPXHARZVGRE-QFWQFVLDSA-N

物化性质

• 沸点：
  548.0±50.0 °C(Predicted)
• 密度：
  0.968±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  31
• 可旋转键数：
  21
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  77
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl (2S,3R,4E)-1-hydroxy-3-(methoxymethoxy)octadec-4-en-2-yl-carbamate 在 水 、 三氟乙酸 作用下， 生成 D-鞘氨醇
  参考文献：
  名称：

  A short enantiodivergent synthesis of d-erythro and l-threo sphingosine

  摘要：

  A new, short (6 steps) and efficient enantiodivergent route to both D-erythro and L threo-sphingosine I and II is disclosed. The high diastereoselection (100% de) reached in the creation of the C-3 stereocenter relies on the use of a sulfoxide as chiral controlling agent in the reduction of the common precursor beta-keto sulfoxide 3. The desired E-alkene of sphingosines has been constructed by the Schlosser modification of the Wittig reaction between aldehyde 8 and the phosphoniun salt 9. The reported methodology can easily be extended to the synthesis of a large number of optically pure syn and anti amino alcohols starting from commercially available amino acids. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01112-0
• 作为产物：
  描述：

  (S)-(-)-3-BOC-4-甲氧羰基-2,2-二甲基-1,3-恶唑烷 在 2,3,5-三甲基吡啶 、 草酰氯 、 水 、 sodium hydride 、 二异丁基氢化铝 、 溶剂黄146 、 二甲基亚砜 、 苯基锂 、 三乙胺 、 三氟乙酸酐 、 lithium bromide 作用下， 以 四氢呋喃 、 乙醚 、 甲苯 、 乙腈 为溶剂， 反应 0.5h， 生成 tert-butyl (2S,3R,4E)-1-hydroxy-3-(methoxymethoxy)octadec-4-en-2-yl-carbamate
  参考文献：
  名称：

  A short enantiodivergent synthesis of d-erythro and l-threo sphingosine

  摘要：

  A new, short (6 steps) and efficient enantiodivergent route to both D-erythro and L threo-sphingosine I and II is disclosed. The high diastereoselection (100% de) reached in the creation of the C-3 stereocenter relies on the use of a sulfoxide as chiral controlling agent in the reduction of the common precursor beta-keto sulfoxide 3. The desired E-alkene of sphingosines has been constructed by the Schlosser modification of the Wittig reaction between aldehyde 8 and the phosphoniun salt 9. The reported methodology can easily be extended to the synthesis of a large number of optically pure syn and anti amino alcohols starting from commercially available amino acids. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01112-0

文献信息

• Caged Ceramide 1-Phosphate Analogues: Synthesis and Properties
  作者：Ravi S. Lankalapalli、Alberto Ouro、Lide Arana、Antonio Gómez-Muñoz、Robert Bittman

  DOI：10.1021/jo902076w

  日期：2009.11.20

  phosphate analogues bearing 7-(diethylamino)coumarin (DECM) and 4-bromo-5-hydroxy-2-nitrobenzhydryl (BHNB) groups in a photolabile ester bond were synthesized. The ability of the “caged” ceramide 1-phosphate analogues to release the bioactive parent molecule upon irradiation at 400−500 nm was demonstrated by stimulation of macrophage cell proliferation.

  合成了在光不稳定酯键中带有 7-(二乙氨基) 香豆素 (DECM) 和 4-溴-5-羟基-2-硝基二苯甲基 (BHNB) 基团的鞘脂磷酸酯类似物。通过刺激巨噬细胞增殖证明了“笼养”神经酰胺 1-磷酸类似物在 400-500 nm 照射下释放生物活性母体分子的能力。
• Amplification of a FRET Probe by Lipid-Water Partition for the Detection of Acid Sphingomyelinase in Live Cells
  作者：Thomas Pinkert、David Furkert、Thomas Korte、Andreas Herrmann、Christoph Arenz

  DOI：10.1002/anie.201611706

  日期：2017.3.1

  monitoring of acid sphingomyelinase (ASM) activity is crucial for investigating its role in lipid‐mediated signaling processes. In this study, we synthesized fluorescent phosphosphingolipids capable of FRET by phosphorodichloridate chemistry. These sphingomyelin analogues are substrates for recombinant human ASM and can be used to monitor ASM activity by fluorescence spectroscopy. Incubation with cell lysates

  实时监测酸性鞘磷脂酶（ASM）活性对于研究其在脂质介导的信号传导过程中的作用至关重要。在这项研究中，我们通过二氯化磷化学合成了能够进行FRET的荧光磷酸鞘脂。这些鞘磷脂类似物是重组人ASM的底物，可用于通过荧光光谱监测ASM活性。与野生型和基因敲除小鼠的细胞裂解液一起温育进一步证实了探针裂解是ASM独有的。我们还系统地利用了荧光团的环境敏感性，以实现响应能力的显着提高。该概念将来可能会转移到其他脂质探针。通过双光子激发显微镜对活细胞中的ASM活性进行成像。
• Caged Ceramide-1-Phosphate Derivatives
  申请人：Bittman Robert

  公开号：US20120238018A1

  公开（公告）日：2012-09-20

  The invention relates to novel caged ceramide 1-phosphate (C1P) and the method of using them for delivering C 1 P intracellularly in vitro and in vivo, for research and therapeutic purposes.

  本发明涉及一种新型笼状鞘氨醇1-磷酸酯（C1P）及其在体外和体内内向细胞内输送C1P的方法，用于研究和治疗目的。
• Caged ceramide-1-phosphate derivatives
  申请人：Bittman Robert

  公开号：US09359389B2

  公开（公告）日：2016-06-07

  The invention relates to novel caged ceramide 1-phosphate (C1P), caged ceramide 1-phosphate derivatives(C1P), and the method of using them for delivering C1P intracellularly in vitro and in vivo, for research and therapeutic purposes. Therapeutic purposes include treatment of diseases associated with cell death, such as neurodegerative diseases, including Alzheimer's disease. The disclosed compositions may also be used for wound healing.

  本发明涉及一种新型的笼状鞘氨醇1-磷酸酯（C1P），笼状鞘氨醇1-磷酸酯衍生物（C1P）及其使用方法，用于体外和体内递送C1P，以进行研究和治疗目的。治疗目的包括治疗与细胞死亡有关的疾病，如神经退行性疾病，包括阿尔茨海默病。所披露的组合物还可用于伤口愈合。
• [EN] CAGED CERAMIDE-1-PHOSPHATE DERIVATIVES<br/>[FR] DÉRIVÉS DE CÉRAMIDE-1-PHOSPHATE BLOQUÉ
  申请人：UNIV CITY NEW YORK RES FOUND

  公开号：WO2011056599A3

  公开（公告）日：2011-09-22