1-{(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-4-{[bis-(4-methoxy-phenyl)-phenyl-methyl]-amino}-1H-pyrimidin-2-one | 80594-29-2

• 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: 1-{(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-4-{[bis-(4-methoxy-phenyl)-phenyl-methyl]-amino}-1H-pyrimidin-2-one
• 英文别名: 1-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-hydroxyoxolan-2-yl]-4-[[bis(4-methoxyphenyl)-phenylmethyl]amino]pyrimidin-2-one
• CAS: 80594-29-2
• 化学式: C₅₁H₄₉N₃O₈
• 分子量: 831.965
• InChiKey: YAPJEYYRZQTOQL-PBQAQGAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  62
• 可旋转键数：
  16
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  120
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-{(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-4-{[bis-(4-methoxy-phenyl)-phenyl-methyl]-amino}-1H-pyrimidin-2-one 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 24.5h， 生成
  参考文献：
  名称：

  Functionalization of solid supports with N-unprotected deoxyribonucleosides

  摘要：

  N-Unprotected deoxyribonucleotides were loaded to solid supports via a succinyl or an oxalyl linker. These solid supports were successfully used for oligonucleotide synthesis by the H-phosphonate method without N-protecting groups. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01129-0
• 作为产物：
  描述：

  在 吡啶 、 碳酸氢钠 作用下， 以 水 为溶剂， 反应 3.08h， 生成 1-{(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-4-{[bis-(4-methoxy-phenyl)-phenyl-methyl]-amino}-1H-pyrimidin-2-one
  参考文献：
  名称：

  Functionalization of solid supports with N-unprotected deoxyribonucleosides

  摘要：

  N-Unprotected deoxyribonucleotides were loaded to solid supports via a succinyl or an oxalyl linker. These solid supports were successfully used for oligonucleotide synthesis by the H-phosphonate method without N-protecting groups. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01129-0

文献信息

• Acylphosphonates
  作者：Mitsuo Fujii、Kouji Ozaki、Mitsuo Sekine、Tsujiaki Hata

  DOI：10.1016/s0040-4020(01)81630-6

  日期：1987.1

  synthesized by a new method via dideoxyribonucleoside 2,2,2-trichloroethoxycarbonylphosphonates and aroylphosphonates. The conversion of dideoxyribonucleoside 2,2,2-trichloroethoxycarbonylphosphonates to dideoxyribonucleoside trimethylsilyl phosphites by treatment with Me3SiCl-Zn-acetylacetone proceeded with retention configuration at phosphorus. The silyl phosphite intermediates were converted to the phosphorothioates

  通过二脱氧核糖核苷2,2,2-三氯乙氧基羰基膦酸酯和芳酰基膦酸酯通过新方法合成了脱氧核糖核苷硫代磷酸酯。通过用Me 3 SiCl-Zn-乙酰丙酮处理，将双脱氧核糖核苷2,2,2-三氯乙氧基羰基膦酸酯转化为双脱氧核糖核苷三甲基甲硅烷基亚磷酸酯，在磷处具有保留构型。通过用硫原位处理将亚磷酸甲硅烷基酯中间体转化为硫代磷酸酯。通过n-BuNH 2的作用，很容易将芳酰基从8-11上除去，并通过单质硫处理原位转化为双脱氧核糖核苷硫代磷酸酯中的仅一种非对映异构体（Rp-构型）。
• Solid-Phase Synthesis of (Poly)phosphorylated Nucleosides and Conjugates
  作者：Viktoria Caroline Tonn、Chris Meier

  DOI：10.1002/chem.201101291

  日期：2011.8.22

  Succinyl‐cycloSal‐phosphate triesters of ribo‐ and 2′‐deoxyribonucleosides were attached to aminomethyl polystyrene as an insoluble solid support and reacted with phosphate‐containing nucleophiles yielding nucleoside di‐ and triphosphates, nucleoside diphosphate sugars, and dinucleoside polyphosphates in high purity after cleavage from the solid support. Here, reactive cycloSal‐phosphate triesters were

  核糖基和2'-脱氧核糖核苷的琥珀酰环Sal-磷酸三酯以不溶性固体支持物的形式连接到氨甲基聚苯乙烯上，并与含磷酸的亲核试剂反应，生成高纯度的核苷二和三磷酸核苷，核苷二磷酸糖和二核苷多磷酸。从固体支持物上裂解。在这里，反应性的环状Sal-磷酸盐三酯用作固定试剂，从而为有效合成磷酸化生物分子和磷酸盐桥联的生物共轭物提供了一种普遍适用的方法。
• Transient protection: efficient one-flask syntheses of protected deoxynucleosides
  作者：G. S. Ti、B. L. Gaffney、R. A. Jones

  DOI：10.1021/ja00369a029

  日期：1982.3
• Chemical Synthesis of Oligonucleotides Containing The (6-4) Photoproduct at the Thymine-Cytosine Site and Its Repair By (6-4) Photolyase
  作者：Shigenori Iwai、Toshimi Mizukoshi、Kenichi Hitomi、Takeshi Todo

  DOI：10.1080/07328319908044706

  日期：1999.6

  A phosphoramidite building block of the T(6-4)C photoproduct was synthesized. One of the differences from T(6-4)T was formation of cytosine hydrates by UV irradiation, and the other was acylation of the amino function with the capping reagent. The capping step was omitted to improve the yield of the desired oligonucleotides. Characterization of the (6-4) photolyase using one of the oligonucleotides revealed that this enzyme restores the pyrimidines in T(6-4)C to their original structures.
• Studies on the Chemical Synthesis of Oligonucleotides Containing the (6−4) Photoproduct of Thymine−Cytosine and Its Repair by (6−4) Photolyase
  作者：Toshimi Mizukoshi、Kenichi Hitomi、Takeshi Todo、Shigenori Iwai

  DOI：10.1021/ja982004y

  日期：1998.10.1

  To prepare oligonucleotides containing the pyrimidine(6-4)pyrimidone photoproduct between thymine and cytosine, which is formed more efficiently than any counterpart at other dipyrimidine sites, a dimer building block of this photoproduct was synthesized. Irradiation of thymidylyl(3'-5')deoxycytidine, with protecting groups at the phosphate and the 3'-hydroxyl function, gave a hydrate of cytosine as the main product, and the formation of the (6-4) photoproduct reached a plateau faster than that from the thymidylyl(3'-5')thymidine derivative. After chromatographic purification of the desired (6-4) photoproduct, a phosphoramidite building block was synthesized in three steps. When this compound was used for the usual oligonucleotide assembly on a solid support, it was found that acylation of the amino group of the 5'-pyrimidine component occurred at the capping step. Oligonucleotides were synthesized successfully by omitting the capping steps after coupling of the (6-4) photoproduct unit. These synthetic oligonucleotides were applied to the characterization of the (6-4) photolyase. By HPLC analyses of the photoreactivation product and its nucleoside composition, it was demonstrated that this (6-4) photoproduct was repaired to its original pyrimidine components by this enzyme.