1-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxyphosphonoyloxyoxolan-2-yl]-5-methylpyrimidine-2,4-dione | 116631-73-3

• 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-methoxyphenyl)-phenylmethoxy]methyl]-4-[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxyphosphonoyloxyoxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 116631-73-3
• 化学式: C₆₂H₆₃N₄O₁₅P
• 分子量: 1135.17
• InChiKey: UAICTNJMHNOJRJ-PHRRUMRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.32
• 重原子数：
  82.0
• 可旋转键数：
  22.0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  219.61
• 氢给体数：
  2.0
• 氢受体数：
  19.0

反应信息

• 作为反应物：
  描述：

  1-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxyphosphonoyloxyoxolan-2-yl]-5-methylpyrimidine-2,4-dione 在 1,2,3,4,5,6,7,8-八硫杂环辛烷 作用下， 以 水 为溶剂， 生成
  参考文献：
  名称：

  合成脱氧核糖核苷3'-氢膦酸酯的简便方法

  摘要：

  在亚甲基二磺酰氯存在下，通过氧化膦酰基化反应，用次膦酸处理，将适当保护的5'-O-二甲氧基三苯甲基三苯甲基脱氧核糖核苷衍生物转化为相应的3'-氢膦酸酯。

  DOI：

  10.1016/0040-4039(88)85329-2
• 作为产物：
  描述：

  5'-O-dimethoxytritylthymidine 3'-H-phosphonate 生成 1-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxyphosphonoyloxyoxolan-2-yl]-5-methylpyrimidine-2,4-dione
  参考文献：
  名称：

  STAWINSKI, JACEK;THELIN, MATS;WESTMAN, ERIK;ZAIN, RULA, J. ORG. CHEM., 55,(1990) N1, C. 3503-3506

  摘要：

  DOI：

文献信息

• Studies on aryl H-phosphonates. I. An efficient method for the preparation of deoxyribo- and ribonucleoside 3′-H-phosphonate monoesters by transesterification of diphenyl H-phosphonate
  作者：Jadwiga Jankowska、Michał Sobkowski、Jacek Stawiński、Adam Kraszewski

  DOI：10.1016/s0040-4039(00)76906-1

  日期：1994.5

  A convenient method for the preparation of deoxyribonucleoside and ribonucleoside 3′-H-phosphonate monoesters via transesterification of diphenyl H-phosphonate with suitable protected nucleosides in pyridine is described.

  描述了通过将二苯基H-膦酸酯与合适的受保护的核苷在吡啶中进行酯交换反应来制备脱氧核糖核苷和核糖核苷3'-H-膦酸酯单酯的简便方法。
• Method for liquid-phase synthesis of nucleic acid
  申请人：TAKEDA PHARMACEUTICAL COMPANY LIMITED

  公开号：US10730904B2

  公开（公告）日：2020-08-04

  In this method, an oligonucleotide represented by formula (II) [wherein Y1, Q, Base, r and r′ are each as defined in claim 1] is prepared by using, as a synthesis unit, a novel nucleoside monomer compound represented by formula (I) [wherein X, R1, Y, Base, Z, Ar, R2, R3 and n are each as defined in claim 1]. The novel nucleoside monomer compound is a nucleoside, the base moiety of which is substituted with an aromatic-hydrocarbon-ring-carbonyl or -thiocarbonyl group having at least one hydrophobic group. The method can dispense with column-chromatographic purification in every reaction, and enables base elongation not only in the 3′-direction but also in the 5′-direction, thus attaining efficient liquid-phase mass synthesis of an oligonucleotide.

  在该方法中，使用式(I)代表的新型核苷单体化合物[其中X、R1、Y、Base、Z、Ar、R2、R3和n各自如权利要求1中定义]作为合成单元，制备式(II)代表的寡核苷酸[其中Y1、Q、Base、r和r′各自如权利要求1中定义]。新型核苷单体化合物是一种核苷，其碱基被具有至少一个疏水基团的芳香-烃环-羰基或-硫代羰基取代。该方法在每个反应中都无需柱色谱纯化，不仅可以在 3′方向上进行碱基延伸，还可以在 5′方向上进行碱基延伸，从而实现寡核苷酸的高效液相大规模合成。
• Nucleoside H-phosphonates. 12. Synthesis of nucleoside 3'-(hydrogen phosphonothioate) monoesters via phosphinate intermediates
  作者：Jacek Stawinski、Mats Thelin、Erik Westman、Rula Zain

  DOI：10.1021/jo00298a023

  日期：1990.5
• METHOD FOR LIQUID-PHASE SYNTHESIS OF NUCLEIC ACID
  申请人：TAKEDA PHARMACEUTICAL COMPANY LIMITED

  公开号：US20190135852A1

  公开（公告）日：2019-05-09

  In this method, an oligonucleotide is prepared by using, as a synthesis unit, a novel nucleoside monomer compound represented by formula (I) [wherein X, R 1 , Y, Base, Z, Ar, R 2 , R 3 and n are each as defined in Claim 1 ]. The novel nucleoside monomer compound is a nucleoside, the base moiety of which is substituted with an aromatic-hydrocarbon-ring-carbonyl or -thiocarbonyl group having at least one hydrophobic group. The method can dispense with column-chromatographic purification in every reaction, and enables base elongation not only in the 3′-direction but also in the 5′-direction, thus attaining efficient liquid-phase mass synthesis of an oligonucleotide.