Acetic acid (2R,3R,4S,5S)-3,4-bis-benzyloxy-5-(diethoxy-phosphorylmethyl)-tetrahydro-furan-2-ylmethyl ester | 130372-43-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid (2R,3R,4S,5S)-3,4-bis-benzyloxy-5-(diethoxy-phosphorylmethyl)-tetrahydro-furan-2-ylmethyl ester
• CAS: 130372-43-9
• 化学式: C₂₆H₃₅O₈P
• 分子量: 506.533
• InChiKey: JFIGMPMLUWHIAZ-VEYUFSJPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.75
• 重原子数：
  35.0
• 可旋转键数：
  14.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  89.52
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3R,4S,5S)-3,4-bis-benzyloxy-5-(diethoxy-phosphorylmethyl)-tetrahydro-furan-2-ylmethyl ester 在 palladium on activated charcoal 甲醇 、 三甲基溴硅烷 、 氢气 、 sodium 、 N,N'-羰基二咪唑 作用下， 以 吡啶 、 二氯甲烷 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 生成 5-phospho-α-D-arabinosyl-C-phosphonophosphate
  参考文献：
  名称：

  Stereospecific synthesis of 5-phospho-α-d-arabinosyl-C-phosphonophosphate (pACpp): a stable analogue of the putative mycobacterial cell wall biosynthetic intermediate 5-phospho-d-arabinosyl pyrophosphate (pApp)

  摘要：

  The stereospecific synthesis of 5-phospho-alpha -D-arabinosyl-C-phosphonophosphate (pACpp) from D-glucosamine is described. This compound was evaluated for its ability to serve as a stable analogue of the putative mycobacterial cell wall biosynthetic intermediate 5-phospho-D-arabinosyl pyrophosphate (pApp). The phosphonophosphate proved incapable of interfering with formation of the mycobacterial arabinan precursor decaprenylphospho-arabinose (DpA) in vitro. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00118-6
• 作为产物：
  描述：

  2,5-anhydro-3,4,6-tri-O-benzyl-1-deoxy-1-iodo-D-mannitol 在 硫酸 作用下， 生成 Acetic acid (2R,3R,4S,5S)-3,4-bis-benzyloxy-5-(diethoxy-phosphorylmethyl)-tetrahydro-furan-2-ylmethyl ester
  参考文献：
  名称：

  Stereospecific synthesis of 5-phospho-α-d-arabinosyl-C-phosphonophosphate (pACpp): a stable analogue of the putative mycobacterial cell wall biosynthetic intermediate 5-phospho-d-arabinosyl pyrophosphate (pApp)

  摘要：

  The stereospecific synthesis of 5-phospho-alpha -D-arabinosyl-C-phosphonophosphate (pACpp) from D-glucosamine is described. This compound was evaluated for its ability to serve as a stable analogue of the putative mycobacterial cell wall biosynthetic intermediate 5-phospho-D-arabinosyl pyrophosphate (pApp). The phosphonophosphate proved incapable of interfering with formation of the mycobacterial arabinan precursor decaprenylphospho-arabinose (DpA) in vitro. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00118-6