2,5-脱水-1-脱氧-1-膦酰-D-阿卓糖醇 | 86762-89-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2,5-脱水-1-脱氧-1-膦酰-D-阿卓糖醇
• 英文名称: 2,5-anhydro-1-deoxy-1-phosphono-D-altritol
• 英文别名: ribose-1-α-methylenephosphonate；2,5-Anhydro-1-deoxy-1-phosphonoaltritol；[(2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]methylphosphonic acid
• CAS: 86762-89-2
• 化学式: C₆H₁₃O₇P
• 分子量: 228.139
• InChiKey: DFYLWBCXEJFDNK-KAZBKCHUSA-N

物化性质

• 沸点：
  585.8±60.0 °C(Predicted)
• 密度：
  1.721±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  127
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,5-脱水-1-脱氧-1-膦酰-D-阿卓糖醇 在 吡啶 、 乙酸酐 作用下， 反应 16.0h， 以16 mg的产率得到
  参考文献：
  名称：

  Synthesis of phosphonate and phostone analogues of ribose-1-phosphates

  摘要：

  描述了磷酸核糖-1-磷酸和5-氟-5-脱氧核糖-1-磷酸的磷酸酯类似物的合成。报道了核糖和5-氟-5-脱氧核糖系列的α-和β-磷酸异构体的制备，并报道了每个α-核糖的相应环磷石的合成。这些化合物已被制备用作探究S. cattleya中氟代谢的细节的工具。

  DOI：

  10.3762/bjoc.5.37
• 作为产物：
  描述：

  5-O-三苯甲基-2,3-O-异亚丙基-D-呋喃核糖 在 sodium hydroxide 、 三氟乙酸 作用下， 以 氘代氯仿 、 二氯甲烷 为溶剂， 反应 18.83h， 生成 2,5-脱水-1-脱氧-1-膦酰-D-阿卓糖醇
  参考文献：
  名称：

  2,5-Anhydro-1-deoxy-1-phosphono-D-altritol, an isosteric analog of .alpha.-D-ribofuranose 1-phosphate

  摘要：

  Condensation of tetramethyl methylenebisphosphonate with 2,3-O-isopropylidene-5-O-trityl-D-ribose gave a mixture of 2,5-anhydro-1-deoxy-1-(diethoxyphosphinyl)-2,3 -O-isopropylidene-5-O-trityl-D-altritol and -allitol. Separation of the isomers and deprotection gave 2,5-anhydro-1-deoxy-1-phosphono-D-altritol and -allitol. The former is the stable isosteric methylenephosphonate analogue of alpha-D-ribose 1-phosphate, the ribose donor in nucleoside phosphorylase catalyzed nucleoside biosynthetic reactions. It did not, however, inhibit purine nucleoside phosphorylase at concentrations of 6 mM.

  DOI：

  10.1021/jm00374a028

文献信息

• Synthesis of phosphonate and phostone analogues of ribose-1-phosphates
  作者：Pitak Nasomjai、David O'Hagan、Alexandra M Z Slawin

  DOI：10.3762/bjoc.5.37

  日期：——

  The synthesis of phosphonate analogues of ribose-1-phosphate and 5-fluoro-5-deoxyribose-1-phosphate is described. Preparations of both the α- and β-phosphonate anomers are reported for the ribose and 5-fluoro-5-deoxyribose series and a synthesis of the corresponding cyclic phostones of each α-ribose is also reported. These compounds have been prepared as tools to probe the details of fluorometabolism in S. cattleya.

  描述了磷酸核糖-1-磷酸和5-氟-5-脱氧核糖-1-磷酸的磷酸酯类似物的合成。报道了核糖和5-氟-5-脱氧核糖系列的α-和β-磷酸异构体的制备，并报道了每个α-核糖的相应环磷石的合成。这些化合物已被制备用作探究S. cattleya中氟代谢的细节的工具。
• 2,5-Anhydro-1-deoxy-1-phosphono-D-altritol, an isosteric analog of .alpha.-D-ribofuranose 1-phosphate
  作者：Rich B. Meyer、Thomas E. Stone、Pradipta K. Jesthi

  DOI：10.1021/jm00374a028

  日期：1984.8

  Condensation of tetramethyl methylenebisphosphonate with 2,3-O-isopropylidene-5-O-trityl-D-ribose gave a mixture of 2,5-anhydro-1-deoxy-1-(diethoxyphosphinyl)-2,3 -O-isopropylidene-5-O-trityl-D-altritol and -allitol. Separation of the isomers and deprotection gave 2,5-anhydro-1-deoxy-1-phosphono-D-altritol and -allitol. The former is the stable isosteric methylenephosphonate analogue of alpha-D-ribose 1-phosphate, the ribose donor in nucleoside phosphorylase catalyzed nucleoside biosynthetic reactions. It did not, however, inhibit purine nucleoside phosphorylase at concentrations of 6 mM.