N'-[9-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-oxo-1H-purin-2-yl]-N,N-dimethylmethanimidamide

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: N'-[9-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-oxo-1H-purin-2-yl]-N,N-dimethylmethanimidamide
• 化学式: C₁₃H₁₈N₆O₅
• 分子量: 338.32
• InChiKey: WDAVDBAMSKZBEN-SYZQJQIISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  145
• 氢给体数：
  4
• 氢受体数：
  6

文献信息

• METHOD FOR SYNTHESIZING RIBONUCLEIC ACID H-PHOSPHONATE MONOMER, AND OLIGONUCLEOTIDE SYNTHESIS IN WHICH SAID MONOMER IS USED
  申请人：GeneDesign, Inc.

  公开号：US20200331945A1

  公开（公告）日：2020-10-22

  The present invention pertains to a method for synthesizing a ribonucleic acid H-phosphonate monomer, and a method for performing oligonucleotide synthesis in which said monomer is used. The present invention pertains to a method for manufacturing an inexpensively manufacturable H-phosphonate nucleoside derivative in which selective protection is provided to position 2′ of a ribonucleoside monomer required in RNA oligonucleotide synthesis. The present invention is characterized in that: hydroxyl groups in position 2′ and position 3′, which have slightly different reactivity, are caused to react with an aromatic acyl halide at low temperature to selectively esterify position 2′; and subsequently the hydroxyl group at position 3′ in one pot is captured by a phosphityl group to prevent position 2′ and position 3′ transfer of the acyl group.

  本发明涉及一种合成核糖核酸H-膦酸酯单体的方法，以及一种在其中使用该单体的寡核苷酸合成方法。本发明涉及一种制造成本低廉的H-膦酸酯核苷衍生物的方法，其中对核糖核苷单体的2′位提供选择性保护，该单体在RNA寡核苷酸合成中所需。本发明的特点在于：在低温下使2′位和3′位的羟基（其反应性略有不同）与芳香酰卤反应，选择性地酯化2′位；随后，在同一反应容器中，通过磷酸酯基捕获3′位的羟基，以防止酰基的2′位和3′位转移。
• Method for synthesizing ribonucleic acid H-phosphonate monomer, and oligonucleotide synthesis in which said monomer is used
  申请人：GeneDesign, Inc.

  公开号：US11174279B2

  公开（公告）日：2021-11-16

  The present invention pertains to a method for synthesizing a ribonucleic acid H-phosphonate monomer, and a method for performing oligonucleotide synthesis in which said monomer is used. The present invention pertains to a method for manufacturing an inexpensively manufacturable H-phosphonate nucleoside derivative in which selective protection is provided to position 2′ of a ribonucleoside monomer required in RNA oligonucleotide synthesis. The present invention is characterized in that: hydroxyl groups in position 2′ and position 3′, which have slightly different reactivity, are caused to react with an aromatic acyl halide at low temperature to selectively esterify position 2′; and subsequently the hydroxyl group at position 3′ in one pot is captured by a phosphityl group to prevent position 2′ and position 3′ transfer of the acyl group.

  本发明涉及一种合成核糖核酸 H-膦酸盐单体的方法，以及使用所述单体进行寡核苷酸合成的方法。本发明涉及一种可廉价制造的 H-膦酸核苷衍生物的制造方法，其中对 RNA 寡核苷酸合成中所需的核糖核苷单体的 2′位提供选择性保护。本发明的特点是：使反应活性略有不同的位置 2′和位置 3′上的羟基在低温下与芳香酰基卤化物反应，选择性地酯化位置 2′；然后用磷酸基俘获一锅中位置 3′上的羟基，以防止位置 2′和位置 3′上的酰基转移。
• US9688715B2
  申请人：——

  公开号：US9688715B2

  公开（公告）日：2017-06-27