D-altro-2,5-anhydro-1-deoxy-1-(dimethoxyphosphinyl)-3,4-O-isopropylidene-6-O-tritylhexitol | 90481-99-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: D-altro-2,5-anhydro-1-deoxy-1-(dimethoxyphosphinyl)-3,4-O-isopropylidene-6-O-tritylhexitol
• 英文别名: 2,5-anhydro-1-deoxy-2,3-O-isopropylidene-1-(dimethoxyphosphinyl)-5-O-trityl-D-altritol；(3aR,4S,6R,6aR)-4-(dimethoxyphosphorylmethyl)-2,2-dimethyl-6-(trityloxymethyl)-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole
• CAS: 90481-99-5
• 化学式: C₃₀H₃₅O₇P
• 分子量: 538.577
• InChiKey: YIFBXIBLDAGLHU-HPQIJTKRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.77
• 重原子数：
  38.0
• 可旋转键数：
  10.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  D-altro-2,5-anhydro-1-deoxy-1-(dimethoxyphosphinyl)-3,4-O-isopropylidene-6-O-tritylhexitol 在 三氟乙酸 作用下， 以 氘代氯仿 为溶剂， 反应 0.83h， 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
• 作为产物：
  描述：

  5-O-三苯甲基-2,3-O-异亚丙基-D-呋喃核糖 、 四甲基亚甲基二磷酸酯 以73%的产率得到
  参考文献：
  名称：

  MCCLARD, RONALD W.;WITTE, JOHN F., BIOORG. CHEM., 18,(1990) N, C. 165-178

  摘要：

  DOI：

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。