(4R)-3-[(2S)-4-[[tert-butyl(dimethyl)silyl]oxymethyl]-2-[(4-methoxyphenyl)methoxy]pent-4-enoyl]-4-propan-2-yl-1,3-oxazolidin-2-one | 1160163-82-5

• 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: (4R)-3-[(2S)-4-[[tert-butyl(dimethyl)silyl]oxymethyl]-2-[(4-methoxyphenyl)methoxy]pent-4-enoyl]-4-propan-2-yl-1,3-oxazolidin-2-one
• CAS: 1160163-82-5
• 化学式: C₂₆H₄₁NO₆Si
• 分子量: 491.7
• InChiKey: NRHBJWGUNQSBPT-GOTSBHOMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.55
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  74.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4R)-3-[(2S)-4-[[tert-butyl(dimethyl)silyl]oxymethyl]-2-[(4-methoxyphenyl)methoxy]pent-4-enoyl]-4-propan-2-yl-1,3-oxazolidin-2-one 在 锂硼氢 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 为溶剂， 以92%的产率得到
  参考文献：
  名称：

  Asymmetric Total Synthesis of Pyranicin

  摘要：

  The asymmetric total synthesis of pyranicin (1) is reported. The butenolide ring was constructed via an asymmetric alkylation/ring-closing metathesis strategy. The three stereocenters in the left-hand tetrahydropyran ring were installed by sequential chiral auxiliary-mediated aldol reactions. Closure of the tetrahydropyran and fusion of the alkyl backbone were affected via a sequential ring-closing metathesis-cross-metathesis strategy.

  DOI：

  10.1021/ol900814w
• 作为产物：
  描述：

  tert-butyl((2-(iodomethyl)allyl)oxy)dimethylsilane 、 (R)-(+)-[4-isopropyl-3-(4-methoxybenzyloxy)acetyl]-2-oxazolidinone 在 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 6.0h， 以80%的产率得到(4R)-3-[(2S)-4-[[tert-butyl(dimethyl)silyl]oxymethyl]-2-[(4-methoxyphenyl)methoxy]pent-4-enoyl]-4-propan-2-yl-1,3-oxazolidin-2-one
  参考文献：
  名称：

  Asymmetric Total Synthesis of Pyranicin

  摘要：

  The asymmetric total synthesis of pyranicin (1) is reported. The butenolide ring was constructed via an asymmetric alkylation/ring-closing metathesis strategy. The three stereocenters in the left-hand tetrahydropyran ring were installed by sequential chiral auxiliary-mediated aldol reactions. Closure of the tetrahydropyran and fusion of the alkyl backbone were affected via a sequential ring-closing metathesis-cross-metathesis strategy.

  DOI：

  10.1021/ol900814w

文献信息

• Asymmetric Total Synthesis of Pyranicin
  作者：Michael T. Crimmins、Danielle L. Jacobs

  DOI：10.1021/ol900814w

  日期：2009.6.18

  The asymmetric total synthesis of pyranicin (1) is reported. The butenolide ring was constructed via an asymmetric alkylation/ring-closing metathesis strategy. The three stereocenters in the left-hand tetrahydropyran ring were installed by sequential chiral auxiliary-mediated aldol reactions. Closure of the tetrahydropyran and fusion of the alkyl backbone were affected via a sequential ring-closing metathesis-cross-metathesis strategy.