(4S)-3-((3S)-3-(4-((bis-(tert-butyl)phosphono)methyl)phenyl)-6-(1,1,2,2-tetramethyl-1-silapropoxy)hexanoyl)-4-benzyl-1,3-oxazolidin-2-one | 525575-15-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物
• 英文名称: (4S)-3-((3S)-3-(4-((bis-(tert-butyl)phosphono)methyl)phenyl)-6-(1,1,2,2-tetramethyl-1-silapropoxy)hexanoyl)-4-benzyl-1,3-oxazolidin-2-one
• 英文别名: (4S)-4-benzyl-3-[(3S)-3-[4-[bis[(2-methylpropan-2-yl)oxy]phosphorylmethyl]phenyl]-6-[tert-butyl(dimethyl)silyl]oxyhexanoyl]-1,3-oxazolidin-2-one
• CAS: 525575-15-9
• 化学式: C₃₇H₅₈NO₇PSi
• 分子量: 687.929
• InChiKey: BCKGKUXNQBAYSB-ACHIHNKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.88
• 重原子数：
  47.0
• 可旋转键数：
  14.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  91.37
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (4S)-3-((3S)-3-(4-((bis-(tert-butyl)phosphono)methyl)phenyl)-6-(1,1,2,2-tetramethyl-1-silapropoxy)hexanoyl)-4-benzyl-1,3-oxazolidin-2-one 在 双(三甲基硅烷基)氨基钾 、 2,4,6-三异丙基苯磺酰叠氮化物 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 0.7h， 以35%的产率得到1-((4S)-2-oxo-4-benzyl(1,3-oxazolidin-3-yl))-(2S,3R)-2-azido-3-(4-((bis-(tert-butyl)phosphono)methyl)phenyl)-6-(1,1,2,2-tetramethyl-1-silapropoxy)hexan-1-one
  参考文献：
  名称：

  Synthesis of N -Fmoc 3-(4-(di-( tert -butyl)phosphonomethyl)phenyl)pipecolic acid as a conformationally constrained phosphotyrosyl mimetic suitably protected for peptide synthesis

  摘要：

  Phosphonomethylphenylalanine (Pmp, 2) has shown wide utility as a hydrolytically stable phosphtyrosyl (pTyr, 1) mimetic, particularly in Src homology 2 (SH2) domain-binding peptides. (2S,3R)-3-(4-(phosphonomethyl)phenyl)pipecolic acid (3) represents a variant of Pmp having phi and chi(1) torsion angles constrained through incorporation into the piperidinyl ring structure contained within pipecolic acid. Reported herein is the enantioselective preparation of 3, in an orthogonally protected form (4) suitable for use in peptide synthesis. Stereochemistries at both the 2- and 3-positions are derived inductively from a single chiral center provided by the commercially available Evans chiral auxiliary, (4S)-4-benzyl-1,3-oxazolidin-2-one. Incorporation of 4 into a Grb2 SH2 domain-directed tripeptide (18) showed that Grb2 SH2 domain-binding affinity was reduced relative to the parent Pmp-containing tripeptide (19). Although conformational constraint did not enhance affinity in this case, novel amino acid analogue 4 may serve as a useful tool for the induction of defined phosphotyrosyl geometry in peptides directed at other signal transduction targets. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01421-7
• 作为产物：
  描述：

  3-(3-(4-((bis(tert-butyl)phosphono)methyl)phenyl)prop-2-enoyl)-4(S)-benzyl-1,3-oxazolidin-2-one 在 咪唑 、 copper(I) bromide dimethylsulfide complex 、 硼烷 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.5h， 生成 (4S)-3-((3S)-3-(4-((bis-(tert-butyl)phosphono)methyl)phenyl)-6-(1,1,2,2-tetramethyl-1-silapropoxy)hexanoyl)-4-benzyl-1,3-oxazolidin-2-one
  参考文献：
  名称：

  Synthesis of N -Fmoc 3-(4-(di-( tert -butyl)phosphonomethyl)phenyl)pipecolic acid as a conformationally constrained phosphotyrosyl mimetic suitably protected for peptide synthesis

  摘要：

  Phosphonomethylphenylalanine (Pmp, 2) has shown wide utility as a hydrolytically stable phosphtyrosyl (pTyr, 1) mimetic, particularly in Src homology 2 (SH2) domain-binding peptides. (2S,3R)-3-(4-(phosphonomethyl)phenyl)pipecolic acid (3) represents a variant of Pmp having phi and chi(1) torsion angles constrained through incorporation into the piperidinyl ring structure contained within pipecolic acid. Reported herein is the enantioselective preparation of 3, in an orthogonally protected form (4) suitable for use in peptide synthesis. Stereochemistries at both the 2- and 3-positions are derived inductively from a single chiral center provided by the commercially available Evans chiral auxiliary, (4S)-4-benzyl-1,3-oxazolidin-2-one. Incorporation of 4 into a Grb2 SH2 domain-directed tripeptide (18) showed that Grb2 SH2 domain-binding affinity was reduced relative to the parent Pmp-containing tripeptide (19). Although conformational constraint did not enhance affinity in this case, novel amino acid analogue 4 may serve as a useful tool for the induction of defined phosphotyrosyl geometry in peptides directed at other signal transduction targets. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01421-7