(S)-4-benzyl-3-((2S,3S)-3-(benzyloxy)-4,4-dimethoxy-2-methylbutanoyl)oxazolidin-2-one | 1333067-47-2

• 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: (S)-4-benzyl-3-((2S,3S)-3-(benzyloxy)-4,4-dimethoxy-2-methylbutanoyl)oxazolidin-2-one
• CAS: 1333067-47-2
• 化学式: C₂₄H₂₉NO₆
• 分子量: 427.497
• InChiKey: WWNJLUSPNSSCQS-YYWHXJBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.42
• 重原子数：
  31.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  74.3
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (S)-4-benzyl-3-((2S,3S)-3-(benzyloxy)-4,4-dimethoxy-2-methylbutanoyl)oxazolidin-2-one 在 三乙烯二胺 、 锂硼氢 、 正丁基锂 、 三乙胺 、 三氟乙酸 、 zinc dibromide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 水 、 溶剂黄146 、 二甲基亚砜 为溶剂， 反应 23.0h， 生成
  参考文献：
  名称：

  Direct Entry to Erythronolides via a Cyclic Bis[Allene]

  摘要：

  The complexity and low tractability of antibiotic macrolides pose serious challenges to addressing the problem of resistance through semi- or total synthesis. Here we describe a new strategy involving the preparation of a complex yet tractable macrocycle and the transformation of this macrocycle into a range of erythronolide congeners. These compounds represent valuable sectors of erythromycinoid structure space and constitute intermediates with the potential to provide further purchase in this space. The routes are short. The erythronolides were prepared in three or fewer steps from the macrocycle, which was prepared in a longest linear sequence of 11 steps.

  DOI：

  10.1021/ja207496p
• 作为产物：
  描述：

  (S)-4-苄基-3-丙酰基-2-噁唑烷酮 在 三氟甲磺酸二丁硼 、 三乙胺 、 silver(l) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 (S)-4-benzyl-3-((2S,3S)-3-(benzyloxy)-4,4-dimethoxy-2-methylbutanoyl)oxazolidin-2-one
  参考文献：
  名称：

  Direct Entry to Erythronolides via a Cyclic Bis[Allene]

  摘要：

  The complexity and low tractability of antibiotic macrolides pose serious challenges to addressing the problem of resistance through semi- or total synthesis. Here we describe a new strategy involving the preparation of a complex yet tractable macrocycle and the transformation of this macrocycle into a range of erythronolide congeners. These compounds represent valuable sectors of erythromycinoid structure space and constitute intermediates with the potential to provide further purchase in this space. The routes are short. The erythronolides were prepared in three or fewer steps from the macrocycle, which was prepared in a longest linear sequence of 11 steps.

  DOI：

  10.1021/ja207496p

文献信息

• Macrolide compounds and methods and intermediates useful for their preparation
  申请人：Williams Lawrence J.

  公开号：US08796474B1

  公开（公告）日：2014-08-05

  The present invention provides intermediate compounds and synthetic methods that can be used to prepare complex cyclic compounds including macrolides. The invention also provides cyclic compounds that have useful biological properties such as antiinfective, antiinflammatory, or antitumor properties.

  本发明提供了中间化合物和合成方法，可用于制备包括大环内酯类化合物在内的复杂环状化合物。该发明还提供具有有用生物学性质的环状化合物，如抗感染、抗炎或抗肿瘤性质。