(2S,3R)-allyl 2-([{(9H-fluoren-9-yl)methoxy}carbonyl]amino)-4-(diethoxyphosphoryl)-4,4-difluoro-3-methylbutanoate | 1609462-45-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (2S,3R)-allyl 2-([{(9H-fluoren-9-yl)methoxy}carbonyl]amino)-4-(diethoxyphosphoryl)-4,4-difluoro-3-methylbutanoate
• CAS: 1609462-45-4
• 化学式: C₂₇H₃₂F₂NO₇P
• 分子量: 551.524
• InChiKey: BYQHFHRZPMETKA-KOSHJBKYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.12
• 重原子数：
  38.0
• 可旋转键数：
  13.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 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：

  (2S,3R)-allyl 2-([{(9H-fluoren-9-yl)methoxy}carbonyl]amino)-4-(diethoxyphosphoryl)-4,4-difluoro-3-methylbutanoate 在 三甲基溴硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 14.0h， 以81%的产率得到{(2R,3S)-3-([{(9H-fluoren-9-yl)methoxy}carbonyl]amino)-4-(allyloxy)-1,1-difluoro-2-methyl-4-oxobutyl}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：

  (2S,3R)-allyl 2-{(tert-butoxycarbonyl)amino}-4-(diethoxyphosphoryl)-4,4-difluoro-3-methylbutanoate 在 sodium carbonate 、 三氟乙酸 作用下， 以 乙腈 为溶剂， 反应 2.0h， 生成 (2S,3R)-allyl 2-([{(9H-fluoren-9-yl)methoxy}carbonyl]amino)-4-(diethoxyphosphoryl)-4,4-difluoro-3-methylbutanoate
  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