(S)-2-Benzyloxycarbonylamino-4-(diisopropoxy-phosphoryl)-4-hydroxy-butyric acid benzyl ester | 270570-20-2

• 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)-2-Benzyloxycarbonylamino-4-(diisopropoxy-phosphoryl)-4-hydroxy-butyric acid benzyl ester
• CAS: 270570-20-2
• 化学式: C₂₅H₃₄NO₈P
• 分子量: 507.521
• InChiKey: AZMBXSPFEJQQQV-NQCNTLBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.78
• 重原子数：
  35.0
• 可旋转键数：
  13.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  120.39
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (S)-2-Benzyloxycarbonylamino-4-(diisopropoxy-phosphoryl)-4-hydroxy-butyric acid benzyl ester 在 palladium dihydroxide 氢气 、 对甲苯磺酸 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 20.0h， 生成 (S)-2-Amino-4-(diisopropoxy-phosphoryl)-4-(tetrahydro-pyran-2-yloxy)-butyric acid
  参考文献：
  名称：

  Synthesis of Suitably Protected Hydroxymethylene Phosphonate- and ‘Phosphate Phosphonate’-Analogues of Phosphoserine and their Incorporation into Synthetic Peptides

  摘要：

  Two suitably protected derivatives of phosphoserine 1 have been prepared in which the regular ester-oxygen is replaced by either a hydroxymethylene moiety or by a phosphorylated hydroxymethylene moiety. The second derivative termed 'phosphate phosphonate' 3 yields the hydroxymethylene phosphonate 2 upon enzymatic cleavage of the phosphate. Two peptide sequences containing regular phosphoserine or the new derivatives have been prepared by Fmoc solid phase strategy and were investigated for their potential as substrates or inhibitors of alkaline phosphatase. The peptides should be useful tools for investigations with protein phosphatases and protein kinases. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00044-2
• 作为产物：
  描述：

  2S-苄氧羰酰氨基-4-氧代-丁酸苄酯 、 diisopropyl trimethylsily phosphite 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以66%的产率得到(S)-2-Benzyloxycarbonylamino-4-(diisopropoxy-phosphoryl)-4-hydroxy-butyric acid benzyl ester
  参考文献：
  名称：

  Synthesis of Suitably Protected Hydroxymethylene Phosphonate- and ‘Phosphate Phosphonate’-Analogues of Phosphoserine and their Incorporation into Synthetic Peptides

  摘要：

  Two suitably protected derivatives of phosphoserine 1 have been prepared in which the regular ester-oxygen is replaced by either a hydroxymethylene moiety or by a phosphorylated hydroxymethylene moiety. The second derivative termed 'phosphate phosphonate' 3 yields the hydroxymethylene phosphonate 2 upon enzymatic cleavage of the phosphate. Two peptide sequences containing regular phosphoserine or the new derivatives have been prepared by Fmoc solid phase strategy and were investigated for their potential as substrates or inhibitors of alkaline phosphatase. The peptides should be useful tools for investigations with protein phosphatases and protein kinases. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00044-2