(S)-allyl 2-([{(9H-fluoren-9-yl)methoxy}carbonyl]amino)-3-[4-{(diethoxyphosphoryl)difluoromethyl}phenyl]propanoate | 1609462-46-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-allyl 2-([{(9H-fluoren-9-yl)methoxy}carbonyl]amino)-3-[4-{(diethoxyphosphoryl)difluoromethyl}phenyl]propanoate
• CAS: 1609462-46-5
• 化学式: C₃₂H₃₄F₂NO₇P
• 分子量: 613.595
• InChiKey: IMIRNJVXVYRLMF-LJAQVGFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.18
• 重原子数：
  43.0
• 可旋转键数：
  14.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  100.16
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (S)-allyl 2-([{(9H-fluoren-9-yl)methoxy}carbonyl]amino)-3-[4-{(diethoxyphosphoryl)difluoromethyl}phenyl]propanoate 在 三甲基溴硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 14.0h， 以52%的产率得到(S)-([4-{2-([{(9H-fluoren-9-yl)methoxy}carbonyl]amino)-3-(allyloxy)-3-oxopropyl}phenyl]difluoromethyl)phosphonic acid
  参考文献：
  名称：

  Development of caged non-hydrolyzable phosphoamino acids and application to photo-control of binding affinity of phosphopeptide mimetic to phosphopeptide-recognizing protein

  摘要：

  The design and synthesis of caged non-hydrolyzable phospho-serine, -threonine, and -tyrosine derivatives that generate parent non-hydrolyzable phosphoamino acids, containing a difluoromethylene unit instead of the oxygen of a phosphoester, after UV-irradiation are described. The caged non-hydrolyzable amino acids were incorporated into peptides by standard Fmoc solid-phase peptide synthesis, and the obtained peptides were successfully converted to the parent non-hydrolyzable phosphopeptides by UV-irradiation. Application of the caged non-hydrolyzable phosphoserine-containing peptide to photo-control the binding affinity of the peptide to 14-3-3 beta protein is also reported. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.04.002
• 作为产物：
  描述：

  (S)-allyl 2-{(tert-butoxycarbonyl)amino}-3-[4-{(diethoxyphosphoryl)difluoromethyl}phenyl]propanoate 在 sodium carbonate 、 三氟乙酸 作用下， 以 乙腈 为溶剂， 反应 2.0h， 生成 (S)-allyl 2-([{(9H-fluoren-9-yl)methoxy}carbonyl]amino)-3-[4-{(diethoxyphosphoryl)difluoromethyl}phenyl]propanoate
  参考文献：
  名称：

  Development of caged non-hydrolyzable phosphoamino acids and application to photo-control of binding affinity of phosphopeptide mimetic to phosphopeptide-recognizing protein

  摘要：

  The design and synthesis of caged non-hydrolyzable phospho-serine, -threonine, and -tyrosine derivatives that generate parent non-hydrolyzable phosphoamino acids, containing a difluoromethylene unit instead of the oxygen of a phosphoester, after UV-irradiation are described. The caged non-hydrolyzable amino acids were incorporated into peptides by standard Fmoc solid-phase peptide synthesis, and the obtained peptides were successfully converted to the parent non-hydrolyzable phosphopeptides by UV-irradiation. Application of the caged non-hydrolyzable phosphoserine-containing peptide to photo-control the binding affinity of the peptide to 14-3-3 beta protein is also reported. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.04.002