(R)-N-[(2R)-2-[(2S,4R)-2-tert-butyl-2,4-dimethyl-5-oxo-1,3-dioxolan-4-yl]decan-2-yl]-2-methylpropane-2-sulfinamide | 946842-98-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-N-[(2R)-2-[(2S,4R)-2-tert-butyl-2,4-dimethyl-5-oxo-1,3-dioxolan-4-yl]decan-2-yl]-2-methylpropane-2-sulfinamide
• CAS: 946842-98-4
• 化学式: C₂₃H₄₅NO₄S
• 分子量: 431.681
• InChiKey: BWMGTVVPOXHSMW-CPVANYHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  29
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  83.8
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (R)-N-[(2R)-2-[(2S,4R)-2-tert-butyl-2,4-dimethyl-5-oxo-1,3-dioxolan-4-yl]decan-2-yl]-2-methylpropane-2-sulfinamide 在 盐酸 作用下， 以 甲醇 、 乙醚 为溶剂， 以88%的产率得到(2S,5R)-5-[(2R)-2-aminodecan-2-yl]-2-tert-butyl-2,5-dimethyl-1,3-dioxolan-4-one
  参考文献：
  名称：

  The first synthesis of N,O-protected β2,2,3,3-isoserines bearing two adjacent quaternary stereogenic centers and their corresponding β-lactams

  摘要：

  The reaction of chiral (2S)-enolates of dioxolan-4-ones, derived from lactic and mandelic acids, with (S-R,?)-tert-butyl sulfinyl ketimines, derived from butan-2-one, pentan-2-one, and decan-2-one, afforded conformation ally restrained beta(2,2,3,3) -isoserines bearing two adjacent quaternary stereogenic centers in the form of N-sulfinyl protected 1'-amino-dioxolan-4-ones. The selective acid-induced removal of the sulfinyl protecting group provided the corresponding 1'-aminodioxolanones, whose base-induced cyclization afforded the corresponding chiral tetra-substituted 3-hydroxy-beta-lactams. The synthesis of a dipeptide by reaction coupling between the 1'-aminodioxolanone (2S,5R,1'R)-19 and N,N-dimethylglycine was successfully achieved. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.05.087
• 作为产物：
  描述：

  、 (2S,5S)-2-(tert-butyl)-2,5-dimethyl-1,3-dioxolan-4-one 在 lithium hexamethyldisilazane 、 六甲基磷酰三胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.75h， 生成 (R)-N-[(2S)-2-[(2S,4R)-2-tert-butyl-2,4-dimethyl-5-oxo-1,3-dioxolan-4-yl]decan-2-yl]-2-methylpropane-2-sulfinamide 、 (R)-N-[(2R)-2-[(2S,4R)-2-tert-butyl-2,4-dimethyl-5-oxo-1,3-dioxolan-4-yl]decan-2-yl]-2-methylpropane-2-sulfinamide
  参考文献：
  名称：

  The first synthesis of N,O-protected β2,2,3,3-isoserines bearing two adjacent quaternary stereogenic centers and their corresponding β-lactams

  摘要：

  The reaction of chiral (2S)-enolates of dioxolan-4-ones, derived from lactic and mandelic acids, with (S-R,?)-tert-butyl sulfinyl ketimines, derived from butan-2-one, pentan-2-one, and decan-2-one, afforded conformation ally restrained beta(2,2,3,3) -isoserines bearing two adjacent quaternary stereogenic centers in the form of N-sulfinyl protected 1'-amino-dioxolan-4-ones. The selective acid-induced removal of the sulfinyl protecting group provided the corresponding 1'-aminodioxolanones, whose base-induced cyclization afforded the corresponding chiral tetra-substituted 3-hydroxy-beta-lactams. The synthesis of a dipeptide by reaction coupling between the 1'-aminodioxolanone (2S,5R,1'R)-19 and N,N-dimethylglycine was successfully achieved. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.05.087