(R)-3-[(2R,3S,4S)-3,5-dihydroxy-2,4-dimethylpentanoyl]-4-isopropyl-5,5-diphenyloxazolidin-2-one | 443761-69-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-3-[(2R,3S,4S)-3,5-dihydroxy-2,4-dimethylpentanoyl]-4-isopropyl-5,5-diphenyloxazolidin-2-one
• 英文别名: (R)-3-[(2R,3S,4S)-3,5-dihydroxy-2,4-dimethyl-pentanoyl]-4-isopropyl-5,5-diphenyl-oxazolidin-2-one；(4R)-3-[(2R,3S,4S)-3,5-dihydroxy-2,4-dimethylpentanoyl]-5,5-diphenyl-4-propan-2-yl-1,3-oxazolidin-2-one
• CAS: 443761-69-1
• 化学式: C₂₅H₃₁NO₅
• 分子量: 425.525
• InChiKey: FKRWFZDLMCKDQK-GKJHBJHPSA-N

物化性质

• 熔点：
  103.5-104.5 °C(Solv: methylcyclohexane (108-87-2))
• 沸点：
  623.4±55.0 °C(Predicted)
• 密度：
  1.194±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  87.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-3-[(2R,3S,4S)-3,5-dihydroxy-2,4-dimethylpentanoyl]-4-isopropyl-5,5-diphenyloxazolidin-2-one 在 2,6-二甲基吡啶 、 二氯乙酸 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 6.25h， 生成 (2R,3S,4S)-3-[(tert-butyldimethylsilanyl)oxy]-5-hydroxy-2,4-dimethylpentanoic acid methoxymethyl amide
  参考文献：
  名称：

  A Practical Building Block for the Synthesis of Discodermolide

  摘要：

  A new highly diastereoselective and practical route to the lactone 6a which is used as a key building block for the total synthesis of the microtubule-stabilizing anticancer agent discodermolide is reported. This exploits the chiral auxiliary (4R)4-isopropyl-5,5-diphenyloxazolidin-2-one (7) which conveys crystallinity to the synthetic intermediates throughout the entire process. Purifications can thus be performed by recrystallization, avoiding chromatography to afford the final product in high enantiomeric purity. The overall efficiency is augmented by the facile recovery of the auxiliary by precipitation at the end of the sequence.

  DOI：

  10.1021/op049950l
• 作为产物：
  描述：

  (4R)-N-Propionyl-5,5-diphenyl-4-isopropyloxazolidin-2-one 在 2,3-二甲基-2-丁基硼烷 、 三氟甲磺酸二丁硼 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 21.67h， 生成 (R)-3-[(2R,3S,4S)-3,5-dihydroxy-2,4-dimethylpentanoyl]-4-isopropyl-5,5-diphenyloxazolidin-2-one
  参考文献：
  名称：

  A Practical Building Block for the Synthesis of Discodermolide

  摘要：

  A new highly diastereoselective and practical route to the lactone 6a which is used as a key building block for the total synthesis of the microtubule-stabilizing anticancer agent discodermolide is reported. This exploits the chiral auxiliary (4R)4-isopropyl-5,5-diphenyloxazolidin-2-one (7) which conveys crystallinity to the synthetic intermediates throughout the entire process. Purifications can thus be performed by recrystallization, avoiding chromatography to afford the final product in high enantiomeric purity. The overall efficiency is augmented by the facile recovery of the auxiliary by precipitation at the end of the sequence.

  DOI：

  10.1021/op049950l

文献信息

• [EN] SYNTHESIS OF DISCODERMOLIDE<br/>[FR] SYNTHESE DU DISCODERMOLIDE
  申请人：NOVARTIS AG

  公开号：WO2004009574A1

  公开（公告）日：2004-01-29

  The invention relates to a process for preparing discodermolide, for preparing intermediates for the manufacture of discodermolide and discodermolide analogues and to the intermediates obtained during the process. Wherein the process proceeds via a tetraene of formula (IV).

  该发明涉及一种制备discodermolide的过程，用于制备制造discodermolide和discodermolide类似物的中间体，以及在过程中获得的中间体。其中，该过程通过式（IV）的四烯体进行。
• PROCESS FOR PREPARING INTERMEDIATES FOR THE MANUFACTURE OF DISCODERMOLIDE AND DISCODERMOLIDE ANALOGUES
  申请人：Novartis AG

  公开号：EP1368334B1

  公开（公告）日：2007-09-05
• A Practical Building Block for the Synthesis of Discodermolide
  作者：Olivier Loiseleur、Guido Koch、Trixie Wagner

  DOI：10.1021/op049950l

  日期：2004.7.1

  A new highly diastereoselective and practical route to the lactone 6a which is used as a key building block for the total synthesis of the microtubule-stabilizing anticancer agent discodermolide is reported. This exploits the chiral auxiliary (4R)4-isopropyl-5,5-diphenyloxazolidin-2-one (7) which conveys crystallinity to the synthetic intermediates throughout the entire process. Purifications can thus be performed by recrystallization, avoiding chromatography to afford the final product in high enantiomeric purity. The overall efficiency is augmented by the facile recovery of the auxiliary by precipitation at the end of the sequence.