(S)-2-{(S)-1-[4-(tert-Butoxy-methyl-phosphinoylmethyl)-phenyl]-allyl}-succinic acid 4-tert-butyl ester | 857083-13-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: (S)-2-{(S)-1-[4-(tert-Butoxy-methyl-phosphinoylmethyl)-phenyl]-allyl}-succinic acid 4-tert-butyl ester
• 英文别名: (2S,3S)-3-[4-[[methyl-[(2-methylpropan-2-yl)oxy]phosphoryl]methyl]phenyl]-2-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]pent-4-enoic acid
• CAS: 857083-13-7
• 化学式: C₂₃H₃₅O₆P
• 分子量: 438.501
• InChiKey: VVDJYHQISQLQCV-YZEIVILOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  30
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  89.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-2-{(S)-1-[4-(tert-Butoxy-methyl-phosphinoylmethyl)-phenyl]-allyl}-succinic acid 4-tert-butyl ester 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 N-羟基-7-氮杂苯并三氮唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 96.0h， 生成 [(E)-(9S,10S,14R,18S)-10-[4-(tert-Butoxy-methyl-phosphinoylmethyl)-phenyl]-18-carbamoylmethyl-14-(5-methyl-indol-1-ylmethyl)-8,17,20-trioxo-7,16,19-triaza-spiro[5.14]icos-11-en-9-yl]-acetic acid tert-butyl ester
  参考文献：
  名称：

  Examination of Phosphoryl-Mimicking Functionalities within a Macrocyclic Grb2 SH2 Domain-Binding Platform

  摘要：

  Reported herein are the design, synthesis, and Grb2 SH2 domain-binding affinities of several phosphoryl-mimicking groups displayed within the context of a conformationally constrained macrocyclic platform. With use of surface plasmon resonance techniques, single-digit nanomolar affinities were exhibited by phosphonic acid and malonyl-containing diacidic phosphoryl mimetics (for 4h and 4g, K-D = 1.47 and 3.62 nM, respectively). Analogues containing monoacidic phosphoryl mimetics provided affinities of K-D = 16-67 nM. Neutral phosphoryl-mimicking groups did not show appreciable binding.

  DOI：

  10.1021/jm050059m
• 作为产物：
  描述：

  Methyl-{4-[(E)-3-oxo-3-((S)-2-oxo-4-phenyl-oxazolidin-3-yl)-propenyl]-benzyl}-phosphinic acid tert-butyl ester 在 lithium hydroxide 、 双氧水 、 苯硫酚铜(I) 、 三氟乙酸 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 9.6h， 生成 (S)-2-{(S)-1-[4-(tert-Butoxy-methyl-phosphinoylmethyl)-phenyl]-allyl}-succinic acid 4-tert-butyl ester
  参考文献：
  名称：

  Examination of Phosphoryl-Mimicking Functionalities within a Macrocyclic Grb2 SH2 Domain-Binding Platform

  摘要：

  Reported herein are the design, synthesis, and Grb2 SH2 domain-binding affinities of several phosphoryl-mimicking groups displayed within the context of a conformationally constrained macrocyclic platform. With use of surface plasmon resonance techniques, single-digit nanomolar affinities were exhibited by phosphonic acid and malonyl-containing diacidic phosphoryl mimetics (for 4h and 4g, K-D = 1.47 and 3.62 nM, respectively). Analogues containing monoacidic phosphoryl mimetics provided affinities of K-D = 16-67 nM. Neutral phosphoryl-mimicking groups did not show appreciable binding.

  DOI：

  10.1021/jm050059m

文献信息

• Examination of Phosphoryl-Mimicking Functionalities within a Macrocyclic Grb2 SH2 Domain-Binding Platform
  作者：Sang-Uk Kang、Zhen-Dan Shi、Karen M. Worthy、Lakshman K. Bindu、Pathirage G. Dharmawardana、Sarah J. Choyke、Donald P. Bottaro、Robert J. Fisher、Terrence R. Burke

  DOI：10.1021/jm050059m

  日期：2005.6.1

  Reported herein are the design, synthesis, and Grb2 SH2 domain-binding affinities of several phosphoryl-mimicking groups displayed within the context of a conformationally constrained macrocyclic platform. With use of surface plasmon resonance techniques, single-digit nanomolar affinities were exhibited by phosphonic acid and malonyl-containing diacidic phosphoryl mimetics (for 4h and 4g, K-D = 1.47 and 3.62 nM, respectively). Analogues containing monoacidic phosphoryl mimetics provided affinities of K-D = 16-67 nM. Neutral phosphoryl-mimicking groups did not show appreciable binding.