(3S,5S,6R)-4-(benzyloxycarbonyl)-5,6-diphenyl-3-[4'-(di-tert-butylphosphonomethyl)benzyl]-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one | 597564-62-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (3S,5S,6R)-4-(benzyloxycarbonyl)-5,6-diphenyl-3-[4'-(di-tert-butylphosphonomethyl)benzyl]-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one
• 英文别名: benzyl (3S,5S,6R)-3-[[4-[bis[(2-methylpropan-2-yl)oxy]phosphorylmethyl]phenyl]methyl]-2-oxo-5,6-diphenylmorpholine-4-carboxylate
• CAS: 597564-62-0
• 化学式: C₄₀H₄₆NO₇P
• 分子量: 683.781
• InChiKey: WHFUUZOLEMYYLW-QGBCWPEESA-N

物化性质

• 熔点：
  66-68 °C
• 沸点：
  787.2±60.0 °C(Predicted)
• 密度：
  1.188±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  49
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  91.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (3S,5S,6R)-4-(benzyloxycarbonyl)-5,6-diphenyl-3-[4'-(di-tert-butylphosphonomethyl)benzyl]-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one 在 钯 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、2.5 MPa 条件下， 以100%的产率得到L-4-((di-tert-butyl)phosphonomethyl)phenylalanine
  参考文献：
  名称：

  Concise and Enantioselective Synthesis of Fmoc-Pmp(Bu^t)₂-OH and Design of Potent Pmp-Containing Grb2-SH2 Domain Antagonists

  摘要：

  L-Phosphonomethylphenylalanine (L-Pmp) is an important phosphatase-resistant pTyr analogue. A most concise and stereoselective approach to the synthesis of the suitably protected Fmoc-Pmp(Bu-t)(2)-OH was developed in order to incorporate the functionally significant L-Pmp residue into peptides and peptidomimetics efficiently using standard Fmoc protocol. With this key building block, we are able to efficiently synthesize a series of potent Pmp-containing Grb2-SH2 domain antagonists, which can be used as chemotherapeutic leads for the treatment of erbB2-overexpressed breast cancer.

  DOI：

  10.1021/ol035078+
• 作为产物：
  描述：

  二叔丁基亚磷酸盐 在 N-溴代丁二酰亚胺(NBS) 、 sodium hexamethyldisilazane 、 sodium hydride 、 过氧化苯甲酰 作用下， 以 四氢呋喃 、 四氯化碳 、 六甲基磷酰三胺 为溶剂， 反应 26.5h， 生成 (3S,5S,6R)-4-(benzyloxycarbonyl)-5,6-diphenyl-3-[4'-(di-tert-butylphosphonomethyl)benzyl]-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one
  参考文献：
  名称：

  Concise and Enantioselective Synthesis of Fmoc-Pmp(Bu^t)₂-OH and Design of Potent Pmp-Containing Grb2-SH2 Domain Antagonists

  摘要：

  L-Phosphonomethylphenylalanine (L-Pmp) is an important phosphatase-resistant pTyr analogue. A most concise and stereoselective approach to the synthesis of the suitably protected Fmoc-Pmp(Bu-t)(2)-OH was developed in order to incorporate the functionally significant L-Pmp residue into peptides and peptidomimetics efficiently using standard Fmoc protocol. With this key building block, we are able to efficiently synthesize a series of potent Pmp-containing Grb2-SH2 domain antagonists, which can be used as chemotherapeutic leads for the treatment of erbB2-overexpressed breast cancer.

  DOI：

  10.1021/ol035078+