(2R,3R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(((benzyloxy)(hydroxy)phosphoryl)oxy)butanoic acid

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (2R,3R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(((benzyloxy)(hydroxy)phosphoryl)oxy)butanoic acid
• 英文别名: (2R,3R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-[hydroxy(phenylmethoxy)phosphoryl]oxybutanoic acid
• 化学式: C₂₆H₂₆NO₈P
• 分子量: 511.468
• InChiKey: HOFDVXHILSPFNS-MZNJEOGPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  36
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  131
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  、 (2R,3R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(((benzyloxy)(hydroxy)phosphoryl)oxy)butanoic acid 在 N-甲基吗啉 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成
  参考文献：
  名称：

  Divergent Stereoselectivity in Phosphothreonine (pThr)-Catalyzed Reductive Aminations of 3-Amidocyclohexanones

  摘要：

  Phosphothreonine (pThr)-embedded peptide catalysts are found to mediate the reductive amination of 3-amidocyclohexanones with divergent selectivity. The choice of peptide sequence can be used to alter the diastereoselectivity to favor either the cis-product or trans-product, which are obtained in up to 93:7 er. NMR studies and DFT calculations are reported and indicate that both pathways rely on secondary interactions between substrate and catalyst to achieve selectivity. Furthermore, catalysts appear to accomplish a parallel kinetic resolution of the substrates. The facility for phosphopeptides to tune reactivity and access multiple products in reductive aminations may translate to the diversification of complex substrates, such as natural products, at numerous reactive sites.

  DOI：

  10.1021/acs.joc.8b00207