(2R,3R,4S,5R,6S)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-6-methoxyoxane-3,4,5-triol | 290359-93-2

• 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: (2R,3R,4S,5R,6S)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-6-methoxyoxane-3,4,5-triol
• CAS: 290359-93-2
• 化学式: C₂₈H₃₂O₈
• 分子量: 496.557
• InChiKey: FLKQFURVUQAKGM-KQZFZZGISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  36
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  107
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S,5R,6S)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-6-methoxyoxane-3,4,5-triol 在 吡啶 、 ammonium cerium(IV) nitrate 作用下， 以 丙酮 为溶剂， 反应 4.0h， 以94%的产率得到Α-D-乳酸吡喃糖苷甲酯
  参考文献：
  名称：

  Ceric Ammonium Nitrate/Pyridine：一种温和的试剂，用于在酸不稳定保护基团的存在下对环状缩醛和缩酮进行选择性脱保护

  摘要：

  试剂系统硝酸铈铵/吡啶可以进行一级和（在某些情况下）二级丙酮化物、亚苄基和四氢吡喃基醚的裂解。反应系统的温和酸性 (pH 4.4) 允许在几个酸不稳定保护基团的存在下进行脱保护。

  DOI：

  10.1055/s-2002-34225
• 作为产物：
  描述：

  4,4'-双甲氧基三苯甲基氯 、 Α-D-乳酸吡喃糖苷甲酯 在 三乙胺 作用下， 以 吡啶 为溶剂， 反应 16.0h， 生成 (2R,3R,4S,5R,6S)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-6-methoxyoxane-3,4,5-triol
  参考文献：
  名称：

  寡糖的固相合成

  摘要：

  描述了一种使用新型不溶性载体（聚乙二醇和聚苯乙烯的共聚物）的高效，立体控制的寡糖固相化学合成方法。测试了几种路易斯酸作为二聚体13形成中用作糖基供体的三氯乙酰亚氨酸酯12的活化剂。

  DOI：

  10.1016/0040-4039(96)01020-9

文献信息

• Synthesis of multi-galactose-conjugated 2′-O-methyl oligoribonucleotides and their in vivo imaging with positron emission tomography
  作者：Jussi Mäkilä、Satish Jadhav、Anu Kiviniemi、Meeri Käkelä、Heidi Liljenbäck、Päivi Poijärvi-Virta、Tiina Laitala-Leinonen、Harri Lönnberg、Anne Roivainen、Pasi Virta

  DOI：10.1016/j.bmc.2014.10.034

  日期：2014.12

  Ga-68 labelled 20-O-methyl oligoribonucleotides (anti-miR-15b) bearing one, three or seven D-galactopyranoside residues have been prepared and their distribution in healthy rats has been studied by positron emission tomography (PET). To obtain the heptavalent conjugate, an appropriately protected 1,4, 7-triazacyclononane-1,4,7-triacetic acid (NOTA) precursor bearing a 4-[4-(4,4'-dimethoxytrityloxy) butoxy] phenyl side arm was first immobilized via a base labile linker to the support and the oligonucleotide was assembled on the detritylated hydroxyl function of this handle. A phosphoramidite building block bearing two phthaloyl protected aminooxy groups and one protected hydroxyl function was introduced into the 5'-terminus. One acetylated galactopyranoside was coupled as a phosphoramidite to the hydroxyl function, the phthaloyl protections were removed on-support and two trivalent galactopyranoside clusters were attached as aldehydes by on-support oximation. A two-step cleavage with aqueous alkali and ammonia released the conjugate in a fully deprotected form, allowing radiolabelling with Ga-68 in solution. The mono-and tri-galactose conjugates were obtained in a closely related manner. In vivo imaging in rats with PET showed remarkable galactose-dependent liver targeting of the conjugates. (C) 2014 Elsevier Ltd. All rights reserved.