(2S,3S)-2-(1-Benzyloxymethyl-vinyl)-3-(4-methoxy-benzyloxymethyl)-oxirane | 315718-83-3

• 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: (2S,3S)-2-(1-Benzyloxymethyl-vinyl)-3-(4-methoxy-benzyloxymethyl)-oxirane
• 英文别名: (2S,3S)-2-[(4-methoxyphenyl)methoxymethyl]-3-(3-phenylmethoxyprop-1-en-2-yl)oxirane
• CAS: 315718-83-3
• 化学式: C₂₁H₂₄O₄
• 分子量: 340.419
• InChiKey: NDCXMWXQPNZAQB-SFTDATJTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  40.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3S)-2-(1-Benzyloxymethyl-vinyl)-3-(4-methoxy-benzyloxymethyl)-oxirane 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 三异丙基亚磷酸酯 、 sodium naphthalenide 作用下， 以 四氢呋喃 、 乙二醇二甲醚 为溶剂， 反应 0.75h， 生成 (4S,5R)-4-(1-benzyloxymethylvinyl)-5-(4-methoxybenzyloxymethyl)-oxazolidin-2-one
  参考文献：
  名称：

  A Regio- and Stereodivergent Synthesis of vic-Amino Alcohols

  摘要：

  [GRAPHICS]A regio- and stereodivergent synthesis of vic-amino alcohols starting from vinylepoxides is described. The developed strategy focuses on the propensity of vinylepoxides and vinylaziridines to be ring-opened at the allylic position by suitable nucleophiles and makes use of reactions that perform such tasks selectively with either retention or inversion of configuration.

  DOI：

  10.1021/ol006736i
• 作为产物：
  描述：

  4-甲氧基氯苄 、 (2S,3S)-(3-(1-(benzyloxy)prop-2-en-2-yl)oxiran-2-yl)methanol 在 sodium hydride 作用下， 以78%的产率得到(2S,3S)-2-(1-Benzyloxymethyl-vinyl)-3-(4-methoxy-benzyloxymethyl)-oxirane
  参考文献：
  名称：

  A Regio- and Stereodivergent Route to All Isomers of vic-Amino Alcohols

  摘要：

  Vicinal amino alcohols are substructures in several important natural products. They are also frequently employed ligands in asymmetric synthesis. Many enantioselective syntheses of vic-amino alcohols have been reported, but each structure has required its own synthetic route. This study presents a synthetic strategy leading to all eight possible isomers of a given beta-amino alcohol, starting from vinyl epoxides. The developed strategy focuses on the propensity of vinyl epoxides and vinylaziridines to be selectively ring-opened at the allylic position by suitable hard nucleophiles. Within this strategy, a novel large-scale aminolysis reaction and the synthesis of a trisubstituted N-H vinylaziridine are detailed.

  DOI：

  10.1021/jo0262053

文献信息

• A Regio- and Stereodivergent Synthesis of <i>v</i><i>ic</i>-Amino Alcohols
  作者：Berit Olofsson、Uttam Khamrai、Peter Somfai

  DOI：10.1021/ol006736i

  日期：2000.12.1

  [GRAPHICS]A regio- and stereodivergent synthesis of vic-amino alcohols starting from vinylepoxides is described. The developed strategy focuses on the propensity of vinylepoxides and vinylaziridines to be ring-opened at the allylic position by suitable nucleophiles and makes use of reactions that perform such tasks selectively with either retention or inversion of configuration.
• A Regio- and Stereodivergent Route to All Isomers of <i>v</i><i>ic</i>-Amino Alcohols
  作者：Berit Olofsson、Peter Somfai

  DOI：10.1021/jo0262053

  日期：2002.11.1

  Vicinal amino alcohols are substructures in several important natural products. They are also frequently employed ligands in asymmetric synthesis. Many enantioselective syntheses of vic-amino alcohols have been reported, but each structure has required its own synthetic route. This study presents a synthetic strategy leading to all eight possible isomers of a given beta-amino alcohol, starting from vinyl epoxides. The developed strategy focuses on the propensity of vinyl epoxides and vinylaziridines to be selectively ring-opened at the allylic position by suitable hard nucleophiles. Within this strategy, a novel large-scale aminolysis reaction and the synthesis of a trisubstituted N-H vinylaziridine are detailed.