benzyl (5R)-5-{[(tert-butyldimethylsilyl)oxy]methyl}-2,2-dioxo-1,2,3-oxathiazolidine-3-carboxylate | 1489246-90-3

• 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: benzyl (5R)-5-{[(tert-butyldimethylsilyl)oxy]methyl}-2,2-dioxo-1,2,3-oxathiazolidine-3-carboxylate
• CAS: 1489246-90-3
• 化学式: C₁₇H₂₇NO₆SSi
• 分子量: 401.556
• InChiKey: XGCOEEZTVHFVCB-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.29
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  82.14
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  benzyl (5R)-5-{[(tert-butyldimethylsilyl)oxy]methyl}-2,2-dioxo-1,2,3-oxathiazolidine-3-carboxylate 、 4-nitro-N-(prop-2-yn-1-yl)benzenesulfonamide 在 sodium hydride 、 柠檬酸 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 、 水 为溶剂， 反应 1.17h， 以67%的产率得到benzyl N-[(2S)-3-[(tert-butyldimethylsilyl)oxy]-2-[N-(prop-2'-yn-1'-yl)(4-nitrobenzene)sulfonamido]propyl]carbamate
  参考文献：
  名称：

  Modular, Gold-Catalyzed Approach to the Synthesis of Lead-like Piperazine Scaffolds

  摘要：

  Ring-opening of cyclic sulfamidates with propargylic sulfonamides yielded substrates for a gold-catalyzed cyclization to yield tetrahydropyrazines. Manipulation of the tetrahydropyrazines, by reduction or using multicomponent reactions, yielded piperazine scaffolds in which substitution of the carbon atoms was varied. Such scaffolds may have value in the synthesis of novel screening compounds with lead-like molecular properties.

  DOI：

  10.1021/ol402988s
• 作为产物：
  描述：

  benzyl N-[(2R)-3-[(tert-butyldimethylsilyl)oxy]-2-hydroxypropyl]carbamate 在 咪唑 、 氯化亚砜 、 三乙胺 、 sodium periodate 、 ruthenium(III) trichloride hydrate 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 以92%的产率得到benzyl (5R)-5-{[(tert-butyldimethylsilyl)oxy]methyl}-2,2-dioxo-1,2,3-oxathiazolidine-3-carboxylate
  参考文献：
  名称：

  Modular, Gold-Catalyzed Approach to the Synthesis of Lead-like Piperazine Scaffolds

  摘要：

  Ring-opening of cyclic sulfamidates with propargylic sulfonamides yielded substrates for a gold-catalyzed cyclization to yield tetrahydropyrazines. Manipulation of the tetrahydropyrazines, by reduction or using multicomponent reactions, yielded piperazine scaffolds in which substitution of the carbon atoms was varied. Such scaffolds may have value in the synthesis of novel screening compounds with lead-like molecular properties.

  DOI：

  10.1021/ol402988s