[2-((2R,3R,4S)-3,4-Bis-benzyloxy-5-methoxy-tetrahydro-furan-2-yl)-ethyl]-phosphonic acid diethyl ester | 206986-16-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [2-((2R,3R,4S)-3,4-Bis-benzyloxy-5-methoxy-tetrahydro-furan-2-yl)-ethyl]-phosphonic acid diethyl ester
• CAS: 206986-16-5
• 化学式: C₂₅H₃₅O₇P
• 分子量: 478.522
• InChiKey: WDWNSYOBGUBVFB-DVFNDFDXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.18
• 重原子数：
  33.0
• 可旋转键数：
  14.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  72.45
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  [2-((2R,3R,4S)-3,4-Bis-benzyloxy-5-methoxy-tetrahydro-furan-2-yl)-ethyl]-phosphonic acid diethyl ester 在 三甲基溴硅烷 、 硫酸 作用下， 以 溶剂黄146 为溶剂， 生成 [2-((2R,3R,4S)-3,4-Bis-benzyloxy-5-hydroxy-tetrahydro-furan-2-yl)-ethyl]-phosphonic acid
  参考文献：
  名称：

  Arabinose-5-phosphate oxime vs its methylenephosphonate mimetic as high energy intermediate of the glucosamine-6P synthase catalyzed reaction

  摘要：

  Arabinose-5-phosphate oxime (1) was found to be the most potent competitive inhibitor of the glucosamine-6P synthase sugar si re to date. Stereoselective syn thesis of the hydrolytically stable methylenephosphonate analogue (2) gave, in 9% yield from D-arabinose, a compound exhibiting a 25 fold weaker inhibitory activity. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00263-9
• 作为产物：
  描述：

  sodium salt of tetraethyl methylenediphenylphosphonate 在 platinum(IV) oxide 氢气 作用下， 以 乙醚 、 乙醇 为溶剂， 生成 [2-((2R,3R,4S)-3,4-Bis-benzyloxy-5-methoxy-tetrahydro-furan-2-yl)-ethyl]-phosphonic acid diethyl ester
  参考文献：
  名称：

  Arabinose-5-phosphate oxime vs its methylenephosphonate mimetic as high energy intermediate of the glucosamine-6P synthase catalyzed reaction

  摘要：

  Arabinose-5-phosphate oxime (1) was found to be the most potent competitive inhibitor of the glucosamine-6P synthase sugar si re to date. Stereoselective syn thesis of the hydrolytically stable methylenephosphonate analogue (2) gave, in 9% yield from D-arabinose, a compound exhibiting a 25 fold weaker inhibitory activity. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00263-9