[(2R,3R)-1,4-bis[(4-methylphenyl)sulfonylamino]-3-methylsulfonyloxybutan-2-yl] methanesulfonate

• 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: [(2R,3R)-1,4-bis[(4-methylphenyl)sulfonylamino]-3-methylsulfonyloxybutan-2-yl] methanesulfonate
• 化学式: C₂₀H₂₈N₂O₁₀S₄
• 分子量: 584.714
• InChiKey: ZSFFBNLCVMNDCK-WOJBJXKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  36
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  213
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  [(2R,3R)-1,4-bis[(4-methylphenyl)sulfonylamino]-3-methylsulfonyloxybutan-2-yl] methanesulfonate 在 copper(l) iodide 、 copper(I) bromide dimethylsulfide complex 、 cesium acetate 、 potassium hydroxide 作用下， 以 四氢呋喃 、 水 、 二甲基亚砜 、 苯 为溶剂， 反应 100.0h， 生成 (2S,2'S)-1,1'-ditosyl-1,1',2,2',3,3',4,4'-octahydro-2,2'-biquinoline
  参考文献：
  名称：

  Ring-Opening and -Expansion of 2,2′-Biaziridine: Access to Diverse Enantiopure Linear and Bicyclic Vicinal Diamines

  摘要：

  The chiral pool-derived 1,1'-ditosyl-2,2'-biaziridine has been established as a valuable building block for the divergent synthesis of enantiopure vicinal diamines. Efficient procedures for the regioselective ring opening of the biaziridine with oxygen, sulfur, nitrogen, and carbon nucleophiles are described. The strategic use of nucleophiles bearing pendant functionality allows further elaboration of the acyclic products to a variety of 2,2'-bicyclic-embedded diamines. Desymmetrization of the biaziridine has also been accomplished via the selective monoaddition of organocuprates.

  DOI：

  10.1021/ol502164b
• 作为产物：
  描述：

  (2R,3R)-1,4-di-(4-methylbenzenesulfonamido)-2,3-O-isopropylidene-2,3-butanediol 在 吡啶 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 4.0h， 生成 [(2R,3R)-1,4-bis[(4-methylphenyl)sulfonylamino]-3-methylsulfonyloxybutan-2-yl] methanesulfonate
  参考文献：
  名称：

  Ring-Opening and -Expansion of 2,2′-Biaziridine: Access to Diverse Enantiopure Linear and Bicyclic Vicinal Diamines

  摘要：

  The chiral pool-derived 1,1'-ditosyl-2,2'-biaziridine has been established as a valuable building block for the divergent synthesis of enantiopure vicinal diamines. Efficient procedures for the regioselective ring opening of the biaziridine with oxygen, sulfur, nitrogen, and carbon nucleophiles are described. The strategic use of nucleophiles bearing pendant functionality allows further elaboration of the acyclic products to a variety of 2,2'-bicyclic-embedded diamines. Desymmetrization of the biaziridine has also been accomplished via the selective monoaddition of organocuprates.

  DOI：

  10.1021/ol502164b

文献信息

• Ring-Opening and -Expansion of 2,2′-Biaziridine: Access to Diverse Enantiopure Linear and Bicyclic Vicinal Diamines
  作者：Stephen J. Bailey、Steven M. Wales、Anthony C. Willis、Paul A. Keller

  DOI：10.1021/ol502164b

  日期：2014.8.15

  The chiral pool-derived 1,1'-ditosyl-2,2'-biaziridine has been established as a valuable building block for the divergent synthesis of enantiopure vicinal diamines. Efficient procedures for the regioselective ring opening of the biaziridine with oxygen, sulfur, nitrogen, and carbon nucleophiles are described. The strategic use of nucleophiles bearing pendant functionality allows further elaboration of the acyclic products to a variety of 2,2'-bicyclic-embedded diamines. Desymmetrization of the biaziridine has also been accomplished via the selective monoaddition of organocuprates.