(4S,5R)-4-(3-benzyloxy-(Z)-propenyl)-5-methyl-3-(toluene-4-sulfonyl)-oxazolidin-2-one

• 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: (4S,5R)-4-(3-benzyloxy-(Z)-propenyl)-5-methyl-3-(toluene-4-sulfonyl)-oxazolidin-2-one
• 英文别名: (4S,5R)-5-methyl-3-(4-methylphenyl)sulfonyl-4-[(Z)-3-phenylmethoxyprop-1-enyl]-1,3-oxazolidin-2-one
• 化学式: C₂₁H₂₃NO₅S
• 分子量: 401.483
• InChiKey: BNKWZCVACLJFGC-ZODOCNFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  81.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (2E,4E)-2,4-己二烯-1-醇 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 C₆H₆O₆(C₃H₆)2 Sodium tetraborate decahydrate 、 Oxone 、 三异丙基亚磷酸酯 、 四丁基硫酸氢铵 、 sodium hydride 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 11.5h， 生成 (4S,5R)-4-(3-benzyloxy-(Z)-propenyl)-5-methyl-3-(toluene-4-sulfonyl)-oxazolidin-2-one
  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 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.