(2R,3R)-methyl 3-((R)-1,1-dimethylethylsulfinamido)-2-methyl-3-(thiazol-2-yl)propanoate | 1421236-48-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (2R,3R)-methyl 3-((R)-1,1-dimethylethylsulfinamido)-2-methyl-3-(thiazol-2-yl)propanoate
• CAS: 1421236-48-7
• 化学式: C₁₂H₂₀N₂O₃S₂
• 分子量: 304.434
• InChiKey: LWXMIFDAFQKOFC-IXGDSRDXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.05
• 重原子数：
  19.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  68.29
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  (R)-N-((1R,2R)-3-((S)-4-benzyl-5,5-dimethyl-2-oxooxazolidin-3-yl)-2-methyl-3-oxo-1-(thiazol-2-yl)propyl)-2-methylpropane-2-sulfinamide 在 氨 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以83%的产率得到(2R,3R)-methyl 3-((R)-1,1-dimethylethylsulfinamido)-2-methyl-3-(thiazol-2-yl)propanoate
  参考文献：
  名称：

  Diastereoselective Synthesis of β-Heteroaryl syn-α-Methyl-β-Amino Acid Derivatives via a Double Chiral Auxiliary Approach

  摘要：

  The addition of the SuperQuat enolate to five- and six-membered heterocyclic tert-butyl sulfinimines led to a high syn-selectivity of up to 99:1 in good to excellent yields. The reaction Is tentatively proposed to proceed through an open-chain transition state with the presence of an alpha-heteroatom on the sulfinimine leading to high diastereoselectivities. The adducts were derivatized to beta-amino esters and amides in a facile manner.

  DOI：

  10.1021/ol3033785