O-tert-butyl-O'-β-cyanoethyl-N,N-diisopropylphosphoramidite | 217939-44-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: O-tert-butyl-O'-β-cyanoethyl-N,N-diisopropylphosphoramidite
• 英文别名: 2-cyanoethyl tert-butyl N,N-diisopropylphosphorodiamidite；tert-butyl 2-cyanoethyl N,N-diisopropylphosphoramidite；3-[[Di(propan-2-yl)amino]-[(2-methylpropan-2-yl)oxy]phosphanyl]oxypropanenitrile
• CAS: 217939-44-1
• 化学式: C₁₃H₂₇N₂O₂P
• 分子量: 274.343
• InChiKey: BKVDLSKEDAPRGJ-UHFFFAOYSA-N

物化性质

• 沸点：
  289.0±23.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  45.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  O-tert-butyl-O'-β-cyanoethyl-N,N-diisopropylphosphoramidite 在 四氮唑 叔丁基过氧化氢 作用下， 以 乙腈 为溶剂， 反应 0.03h， 生成 tert-butyl di-(2-cyanoethyl)phosphate
  参考文献：
  名称：

  Phosphoramidites derived from tertiary alcohols. Why do they sometimes couple with low efficiency?

  摘要：

  tert-Alkyl phosphoramidites are somewhat sterically hindered, but give phosphites in good yields with tetrazole catalysis when the coupling time with alcohols is prolonged. Low yields of phosphotriesters are caused by elimination of the tertiary alkyl group during the subsequent oxidation of the phosphite with iodine/water/pyridine, and can be avoided by the use of tert-butyl hydroperoxide as the oxidant. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01844-9
• 作为产物：
  描述：

  双(二异丙基氨基)(2-氰基乙氧基)膦 、 叔丁醇 在 二异丙基铵盐四氮唑 作用下， 以 二氯甲烷 为溶剂， 以65%的产率得到O-tert-butyl-O'-β-cyanoethyl-N,N-diisopropylphosphoramidite
  参考文献：
  名称：

  通过胺与亚磷酸酯的氧化偶联进行固相合成时将化学手柄插入 DNA 主链

  摘要：

  开发了一种在固相合成过程中将化学柄连接到寡核苷酸主链的可行且廉价的方法。通过使用碘的氧化偶联将伯胺或仲胺连接到插入叔丁基亚磷酰胺的位置以获得所需的氨基磷酸酯。通过这种方法，不同的官能团如叠氮化物、炔烃、胺被插入作为化学手柄。

  DOI：

  10.1002/anie.202305373

文献信息

• Modified oligonucleotides and compound that can be used for synthesizing same
  申请人：GUANGZHOU RIBOBIO CO., LTD.

  公开号：US20200369703A1

  公开（公告）日：2020-11-26

  The present disclosure falls within the field of biomedical technology, and in particular relates to modified oligonucleatides and a compound that can be used for synthesizing same and a method for modifying oligonucleotides. The present disclosure also relates to the use of the modified oligonucleotides for preventing and/or treating diseases associated with the liver in a subject.

  本公开涉及生物医学技术领域，特别是涉及改良寡核苷酸和一种可用于合成相同的化合物以及一种修改寡核苷酸的方法。本公开还涉及使用改良寡核苷酸来预防和/或治疗与主体肝脏相关的疾病。
• Preparation of an asymmetrically protected phosphoramidite and its application in solid-phase synthesis of phosphopeptides
  作者：Zoltán Kupihár、Györgyi Váradi、Éva Monostori、Gábor K Tóth

  DOI：10.1016/s0040-4039(00)00615-8

  日期：2000.6

  O-tert-Butyl-O′--cyanoethyl-N,N-diisopropylphosphoramidite as a new global phosphorylation reagent and its application for solid-phase phosphopeptide synthesis via monoprotected phosphate-peptide ester during peptide synthesis are described.

  O-叔丁基- ø '--cyanoethyl- Ñ，Ñ -diisopropylphosphoramidite作为新的全球磷酸化试剂，并在肽合成中描述其为固相磷酸合成单保护的通过磷酸肽酯应用。
• Compounds and methods for the synthesis of 5-(N-protected-tryptaminocarboxyamide)-2′-deoxyuridine phosphoramidite for incorporation into a nucleic acid
  申请人：SOMALOGIC, INC.

  公开号：US10634679B2

  公开（公告）日：2020-04-28

  Modified Tryptamine, Tryptamine-2′-deoxy-uridine (TrpdU) and TrpdU-phosphoramidites for oligonucleotide synthesis are provided, as well as improved methods of their synthesis and oligonucleotides comprising at least one modified TrpdU nucleotide.

  提供了用于寡核苷酸合成的修饰色胺、色胺-2′-脱氧尿苷（TrpdU）和 TrpdU-磷酰胺，以及改进的合成方法和包含至少一种修饰 TrpdU 核苷酸的寡核苷酸。
• S-antigen transport inhibiting oligonucleotide polymers and methods
  申请人：ALIGOS THERAPEUTICS, INC.

  公开号：US11166976B2

  公开（公告）日：2021-11-09

  Various embodiments provide STOPS™ polymers that are S-antigen transport inhibiting oligonucleotide polymers, processes for making them and methods of using them to treat diseases and conditions. In some embodiments the STOPS™ modified oligonucleotides include an at least partially phosphorothioated sequence of alternating A and C units having modifications as described herein. The sequence independent antiviral activity against hepatitis B of embodiments of STOPS™ modified oligonucleotides, as determined by HBsAg Secretion Assay, is greater than that of a reference compound.

  各种实施方案提供了抑制 S 抗原转运的寡核苷酸聚合物 STOPS™、其制造工艺以及用其治疗疾病和病症的方法。在某些实施方案中，STOPS™修饰的寡核苷酸包括至少部分硫代磷酸序列，该序列由具有本文所述修饰的交替 A 和 C 单元组成。通过 HBsAg 分泌测定法确定，STOPS™ 修饰寡核苷酸实施例的序列独立乙型肝炎抗病毒活性高于参比化合物。
• A versatile reagent for the synthesis of 5′-phosphorylated, 5′-thiophosphorylated or 5′-phosphoramidate-conjugated oligonucleotides
  作者：Albert Meyer、Camille Bouillon、Sébastien Vidal、Jean-Jacques Vasseur、François Morvan

  DOI：10.1016/j.tetlet.2006.10.049

  日期：2006.12

  We report the synthesis of a new phosphorylating reagent that is easily accessible and allows not only the chemical synthesis of 5'-phosphorylated and 5'-thiophosphorylated oligonucleotides but also the 5'-conjugation through a phosphoramidate linkage. 5'-Amino-linker and 5'-alkyne oligonucleotides were obtained and the latter was conjugated by a 1,3-dipolar cycloaddition (click chemistry) with a galactosylated azide derivative to afford 5'-galactosyl oligonucleotide with high efficiency. (c) 2006 Elsevier Ltd. All rights reserved.