(R)-4-[2-(4-octylphenyl)ethyl]-4-(3-oxo-1,5-dihydro-3λ⁵-benzo[e][1,3,2]dioxaphosphepin-3-yloxymethyl)oxazolidin-2-one | 863225-37-0

• 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: (R)-4-[2-(4-octylphenyl)ethyl]-4-(3-oxo-1,5-dihydro-3λ⁵-benzo[e][1,3,2]dioxaphosphepin-3-yloxymethyl)oxazolidin-2-one
• 英文别名: (R)-4-[2-(4-octyl-phenyl)-ethyl]-4-(3-oxo-1,5-dihydro-3-lambda*5*-benzo[e][1,3,2]dioxaphosphepin-3-yloxymethyl)-oxazolidin-2-one；(4R)-4-[2-(4-octylphenyl)ethyl]-4-[(3-oxo-1,5-dihydro-2,4,3lambda5-benzodioxaphosphepin-3-yl)oxymethyl]-1,3-oxazolidin-2-one；(4R)-4-[2-(4-octylphenyl)ethyl]-4-[(3-oxo-1,5-dihydro-2,4,3λ5-benzodioxaphosphepin-3-yl)oxymethyl]-1,3-oxazolidin-2-one
• CAS: 863225-37-0
• 化学式: C₂₈H₃₈NO₆P
• 分子量: 515.587
• InChiKey: PNWRXMYOUVUBLV-MUUNZHRXSA-N

物化性质

• 沸点：
  678.8±50.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  36
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (R)-4-[2-(4-octylphenyl)ethyl]-4-(3-oxo-1,5-dihydro-3λ⁵-benzo[e][1,3,2]dioxaphosphepin-3-yloxymethyl)oxazolidin-2-one 在 palladium on activated charcoal 氢氧化钾 、 lithium hydroxide 、 乙二胺四乙酸 、 氢气 、 硼酸 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 26.5h， 生成 phosphoric acid mono[(R)-2-hydroxymethyl-4-(4-octylphenyl)-2-(1-oxo-1,3-dihydroisoindol-2-yl)butyl]ester
  参考文献：
  名称：

  Novel Immunomodulator FTY720 Is Phosphorylated in Rats and Humans To Form a Single Stereoisomer. Identification, Chemical Proof, and Biological Characterization of the Biologically Active Species and Its Enantiomer

  摘要：

  In vivo phosphorylation. of FTY720 (1) in rats and humans resulted exclusively in the biologically active (S)-configured enantiomer, which was proven by an ex vivo o-phthaldialdehyde derivatization protocol especially elaborated for phosphates of 1. Starting from the prochiral amino alcohol 1, racemic and enantiomerically pure phosphates of 1 were synthesized. Pure enantiomers were obtained after purification of a partially protected key intermediate on an enantioselective support. The absolute stereochemistry was determined by X-ray diffraction.

  DOI：

  10.1021/jm050242f
• 作为产物：
  描述：

  2-氨基-2-[2-(4-辛基苯基)乙基]-1,3-丙二醇 在 四氮唑 、 sodium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 67.5h， 生成 (R)-4-[2-(4-octylphenyl)ethyl]-4-(3-oxo-1,5-dihydro-3λ⁵-benzo[e][1,3,2]dioxaphosphepin-3-yloxymethyl)oxazolidin-2-one
  参考文献：
  名称：

  Novel Immunomodulator FTY720 Is Phosphorylated in Rats and Humans To Form a Single Stereoisomer. Identification, Chemical Proof, and Biological Characterization of the Biologically Active Species and Its Enantiomer

  摘要：

  In vivo phosphorylation. of FTY720 (1) in rats and humans resulted exclusively in the biologically active (S)-configured enantiomer, which was proven by an ex vivo o-phthaldialdehyde derivatization protocol especially elaborated for phosphates of 1. Starting from the prochiral amino alcohol 1, racemic and enantiomerically pure phosphates of 1 were synthesized. Pure enantiomers were obtained after purification of a partially protected key intermediate on an enantioselective support. The absolute stereochemistry was determined by X-ray diffraction.

  DOI：

  10.1021/jm050242f

文献信息

• [EN] AMINOPROPANOL DERIVATIVES<br/>[FR] DERIVES D'AMINOPROPANOL
  申请人：NOVARTIS AG

  公开号：WO2005021503A1

  公开（公告）日：2005-03-10

  Compounds of formula (I): wherein R1, R2, n and m are as defined in the specification, processes for their production, their uses and pharmaceutical compositions containing them.

  式（I）的化合物：其中R1、R2、n和m如规范中定义，它们的生产过程，它们的用途以及含有它们的药物组合物。
• Novel Immunomodulator FTY720 Is Phosphorylated in Rats and Humans To Form a Single Stereoisomer. Identification, Chemical Proof, and Biological Characterization of the Biologically Active Species and Its Enantiomer
  作者：Rainer Albert、Klaus Hinterding、Volker Brinkmann、Danilo Guerini、Constanze Müller-Hartwieg、Helmut Knecht、Corinne Simeon、Markus Streiff、Trixie Wagner、Karl Welzenbach、Frédéric Zécri、Markus Zollinger、Nigel Cooke、Eric Francotte

  DOI：10.1021/jm050242f

  日期：2005.8.1

  In vivo phosphorylation. of FTY720 (1) in rats and humans resulted exclusively in the biologically active (S)-configured enantiomer, which was proven by an ex vivo o-phthaldialdehyde derivatization protocol especially elaborated for phosphates of 1. Starting from the prochiral amino alcohol 1, racemic and enantiomerically pure phosphates of 1 were synthesized. Pure enantiomers were obtained after purification of a partially protected key intermediate on an enantioselective support. The absolute stereochemistry was determined by X-ray diffraction.