N-phenyl-5,6-dihydroxy-perhydro-4,7-epoxy-isoindole-1,3-dione | 1070908-85-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: N-phenyl-5,6-dihydroxy-perhydro-4,7-epoxy-isoindole-1,3-dione
• 英文别名: N-phenyl-5,6-dihydroxy-hexahydro-4,7-epoxyisobenzopyrrole-1,3-dione；(4R,5S,6R,7S)-5,6-dihydroxy-2-phenyl-3a,4,5,6,7,7a-hexahydro-4,7-epoxyisoindole-1,3-dione
• CAS: 1070908-85-8
• 化学式: C₁₄H₁₃NO₅
• 分子量: 275.261
• InChiKey: DQQIQBGIEFFYBA-TZGWRFBESA-N

物化性质

• 沸点：
  599.0±50.0 °C(Predicted)
• 密度：
  1.593±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.71
• 重原子数：
  20.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  87.07
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N-phenyl-5,6-dihydroxy-perhydro-4,7-epoxy-isoindole-1,3-dione 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 N-phenyl-5-(4,4'-dimethoxytriphenylmethoxy)-6-[2-carboxypropanoyloxy]-hexahydro-4,7-epoxyisoindole-1,3-dione triethylamine salt
  参考文献：
  名称：

  Convenient Large‐Scale Synthesis of Universal Solid Support

  摘要：

  A simple, convenient large-scale synthesis of a universal solid support useful for the synthesis of oligonucleotides is described.

  DOI：

  10.1080/00397910600639638
• 作为产物：
  描述：

  N-phenyl-hexahydro-4,7-epoxyisoindole-1,3-dione 在 四氧化锇 、 N-甲基吗啉氧化物 作用下， 以 水 、 丙酮 、 叔丁醇 为溶剂， 反应 4.0h， 以90%的产率得到N-phenyl-5,6-dihydroxy-perhydro-4,7-epoxy-isoindole-1,3-dione
  参考文献：
  名称：

  UnyLinker二聚体杂质表征和工艺改进

  摘要：

  本文中，我们描述了UnyLinker二聚体的分离和表征，该二聚体如果不受控制，可以掺入寡核苷酸产物中。二聚体是由于异常的分子间ether催化的醚化作用而形成的。我们证明，通过简单地用NMO代替H 2 O 2作为助氧化剂，不会形成UnyLinker二聚体杂质。

  DOI：

  10.1016/j.tetlet.2017.01.101

文献信息

• Universal building blocks and support media for synthesis of oligonucleotides and their analogs
  申请人：——

  公开号：US20040152905A1

  公开（公告）日：2004-08-05

  Compounds for the synthesis of oligomeric compounds, particularly oligonucleotides and chemically modified oligonucleotide analogs, are provided. In addition, methods for functionalization of a support medium with a first monomeric subunit and methods for the synthesis of oligomeric compounds utilizing the novel compounds bound to support media are provided.

  提供用于合成寡聚化合物，特别是寡核苷酸和化学修饰的寡核苷酸类似物的化合物。此外，还提供了将支持介质功能化为第一单体亚基的方法，以及利用与支持介质结合的新化合物合成寡聚化合物的方法。
• New Cleavable Spacers for Tandem Synthesis of Multiple Oligo­nucleotides
  作者：Yoshiyuki Hari、Kazuki Yamamoto、Yasufumi Fuchi、Masaya Okabe、Takashi Osawa、Yuta Ito

  DOI：10.1055/a-1538-9883

  日期：2021.12

  acquired from a column loaded with a specific solid support. Herein, we have developed new cleavable spacer (CS) derivatives for tandem synthesis of multiple oligonucleotides on a single column­. Four CS analogues were designed, synthesized, and inserted between two oligonucleotide sequences using an automated oligonucleotide synthesizer. The CS derivatives bearing a cyclic cis-1,2-diol exhibited efficient

  在固相寡核苷酸合成中，通常从装有特定固体支持物的柱子中获得单个寡核苷酸。在此，我们开发了新的可切割间隔 (CS) 衍生物，用于在单个柱上串联合成多个寡核苷酸。使用自动寡核苷酸合成仪设计、合成了四种 CS 类似物并插入到两个寡核苷酸序列之间。带有环状 cis-1,2-二醇的 CS 衍生物在常用的氨水碱性条件下表现出两种寡核苷酸的有效释放。在 CS 类似物中，发现具有稳健结构的 CS 可以潜在地用作间隔分子，用于单个序列中多个寡核苷酸的串联合成。
• UnyLinker: An Efficient and Scaleable Synthesis of Oligonucleotides Utilizing a Universal Linker Molecule: A Novel Approach To Enhance the Purity of Drugs
  作者：Vasulinga T. Ravikumar、R. Krishna Kumar、Phil Olsen、Max N. Moore、Recaldo L. Carty、Mark Andrade、Dennis Gorman、Xuefeng Zhu、Isaiah Cedillo、Zhiwei Wang、Lucio Mendez、Anthony N. Scozzari、Gerardo Aguirre、Ratnasamy Somanathan、Sylvain Berneès

  DOI：10.1021/op8000178

  日期：2008.5.1

  A novel universal linker (UnyLinker) molecule which has a conformationally rigid and chemically stable bridge head ring oxygen atom carrying a conventional 4,4'-dimethoxytrityl (DMT) and succinyl groups locked in a syn orientation has been developed to carry out oligonucleotide synthesis efficiently and smoothly. The geometry of the vicinal syn oxygen functionalized group allows fast and clean cleavage under standard aqueous ammonia deprotection conditions to afford high-quality oligonucleotides. No base modification is observed, based on the ion-pair UPLC-UV-MS (IP-HPLC-UV-MS) method with detection limit of <0.1%. A class of impurities formed by branching from the exocyclic amino group of nucleosides loaded onto a solid support has been eliminated by the use of this method. Examples demonstrating the versatile nature of this molecule are shown by syntheses of different chemistries such as 2'-deoxy, 2'-O-methyl, 2'-O-methoxyethyl, Lock nucleic acids (LNA), 2'-alpha-fluoro nucleic acids (FANA), conjugates such as 5'-phosphate monoester and biotin, and phosphate diester and phosphorothioate backbone modifications. This molecule was loaded onto several commercial solid supports and used in both gas-sparged and packed-bed automated DNA/RNA synthesizers. Large-scale syntheses (up to 700 mmol) of multiple phosphorothioate first- and second-generation antisense drugs on GE-Amersham's OligoProcess synthesizer are demonstrated further, showing that this chemistry could be used for efficient synthesis of multiple oligonucleotide drugs using a single raw material, thereby eliminating a difficult to characterize nucleoside-loaded polymer matrix used as a starting material. A mechanism for deprotection and cleavage of the linker molecule to liberate the free oligonucleotide is proposed. Characterization of the cyclic byproduct formed during release of the oligonucleotide is presented. The exo-syn configuration of the dihydroxy structure of the UnyLinker molecule is conclusively established by X-ray crystallography studies. A novel method to remove the last traces of osmium used during the synthesis of the UnyLinker molecule to reach undetectable levels (<1 ppm) is also described.