(4R,5S)-3-benzyl-5-[(1R)-2-[tert-butyl(diphenyl)silyl]oxy-1-hydroxyethyl]-4-ethenyl-1,3-oxazolidin-2-one | 823181-83-5

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (4R,5S)-3-benzyl-5-[(1R)-2-[tert-butyl(diphenyl)silyl]oxy-1-hydroxyethyl]-4-ethenyl-1,3-oxazolidin-2-one
• CAS: 823181-83-5
• 化学式: C₃₀H₃₅NO₄Si
• 分子量: 501.698
• InChiKey: YAOAYZFLJMUVPO-FCEKVYKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  36
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4R,5S)-3-benzyl-5-[(1R)-2-[tert-butyl(diphenyl)silyl]oxy-1-hydroxyethyl]-4-ethenyl-1,3-oxazolidin-2-one 在 四丁基氟化铵 、 silica gel 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 以85%的产率得到(4R,5S)-3-Benzyl-5-((R)-1,2-dihydroxy-ethyl)-4-vinyl-oxazolidin-2-one
  参考文献：
  名称：

  Stereoselective Access to the Versatile 4-Aminohex-5-ene-1,2,3-triol Pattern

  摘要：

  We developed a stereocontrolled route allowing potential access to the eight isomers of 4-benzylaminohex-5-ene-1,2,3-triol in two or four steps and ca. 50% yield from readily available chiral nonracemic cis- or trans-alpha,beta-epoxyimine precursors. A new (NH4)(2)CO3-based carboxylation/intramolecular cyclization sequence allowed regio- and stereocontrolled C-3 epoxide opening while neat C-2 hydrolysis was ensured by simple aqueous acidic treatment.

  DOI：

  10.1021/jo048766v
• 作为产物：
  描述：

  (2S,3R)-4-(tert-butyldiphenylsilyloxy)-2,3-epoxybutan-1-al 在 4 A molecular sieve 、 三氟化硼乙醚 作用下， 以 四氢呋喃 、 乙醚 、 水 为溶剂， 反应 25.0h， 生成 (4R,5S)-3-benzyl-5-[(1R)-2-[tert-butyl(diphenyl)silyl]oxy-1-hydroxyethyl]-4-ethenyl-1,3-oxazolidin-2-one
  参考文献：
  名称：

  Stereoselective Access to the Versatile 4-Aminohex-5-ene-1,2,3-triol Pattern

  摘要：

  We developed a stereocontrolled route allowing potential access to the eight isomers of 4-benzylaminohex-5-ene-1,2,3-triol in two or four steps and ca. 50% yield from readily available chiral nonracemic cis- or trans-alpha,beta-epoxyimine precursors. A new (NH4)(2)CO3-based carboxylation/intramolecular cyclization sequence allowed regio- and stereocontrolled C-3 epoxide opening while neat C-2 hydrolysis was ensured by simple aqueous acidic treatment.

  DOI：

  10.1021/jo048766v

文献信息

• Stereoselective Access to the Versatile 4-Aminohex-5-ene-1,2,3-triol Pattern
  作者：Tahar Ayad、Vanessa Faugeroux、Yves Génisson、Chantal André,、Michel Baltas、Liliane Gorrichon

  DOI：10.1021/jo048766v

  日期：2004.12.1

  We developed a stereocontrolled route allowing potential access to the eight isomers of 4-benzylaminohex-5-ene-1,2,3-triol in two or four steps and ca. 50% yield from readily available chiral nonracemic cis- or trans-alpha,beta-epoxyimine precursors. A new (NH4)(2)CO3-based carboxylation/intramolecular cyclization sequence allowed regio- and stereocontrolled C-3 epoxide opening while neat C-2 hydrolysis was ensured by simple aqueous acidic treatment.