1-[3'-deoxy-4',6'-O-(1,1,3,3-tetraisopropyldisiloxan-1,3-diyl)-β-D-psicofuranosyl]uracil | 105291-41-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1-[3'-deoxy-4',6'-O-(1,1,3,3-tetraisopropyldisiloxan-1,3-diyl)-β-D-psicofuranosyl]uracil
• 英文别名: 1-[(6aR,8S,9aS)-8-(hydroxymethyl)-2,2,4,4-tetra(propan-2-yl)-6,6a,9,9a-tetrahydrofuro[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl]pyrimidine-2,4-dione
• CAS: 105291-41-6
• 化学式: C₂₂H₄₀N₂O₇Si₂
• 分子量: 500.74
• InChiKey: KPNCPWJCFUVZEA-JQVVWYNYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.93
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-[3'-deoxy-4',6'-O-(1,1,3,3-tetraisopropyldisiloxan-1,3-diyl)-β-D-psicofuranosyl]uracil 在 氟化铵 作用下， 以 甲醇 为溶剂， 生成 1'-Pivaloyl-2'-deoxyuridine
  参考文献：
  名称：

  Independent Generation and Reactivity of 2‘-Deoxyurid-1‘-yl

  摘要：

  DOI：

  10.1021/jo951769a
• 作为产物：
  描述：

  在 sodium methylate 、 palladium dichloride 作用下， 以 吡啶 、 甲醇 、 四氯化碳 为溶剂， 生成 1-[3'-deoxy-4',6'-O-(1,1,3,3-tetraisopropyldisiloxan-1,3-diyl)-β-D-psicofuranosyl]uracil
  参考文献：
  名称：

  Ex-NovoandRevisumProcedures for the Preparation of C-1′ Branched Nucleosides

  摘要：

  C-1' acylated derivatives of 2'-deoxyuridine were obtained either by revising the existing procedures or by introducing a new methodology.

  DOI：

  10.1080/15257779908041524

文献信息

• Synthesis of 1′-phenazine-tethered psicofuranosyl oligonucleotides: The thermal stability and fluorescence properties of their duplexes and triplexes
  作者：D. Ossipov、J. Chattopadhyaya

  DOI：10.1016/s0040-4020(98)00237-3

  日期：1998.5

  corresponding 6′-O-DMTr protected 4′-phosphoramidite block 13 in three steps [7 → 9 (83%) → 11 (83%) → 13 (83%)], whereas compound 8 was used in the preparation of the modified solid support 14 in four steps [8 → 10 (28%) → 12 (70%) → 14]. Modified 9-mer ODNs 28 – 31 and 18-mer ODNs 22 – 25 were then assembled in a usual manner using automated solid-phase DNA synthesis protocol. The phenazine-tethered

  描述了在1-（3'-deoxypsicofuranosyl）尿嘧啶的C1'处与吩嗪（pzn）相连的修饰寡核苷酸（ODN）的合成，热稳定性以及其双链体和三链体的荧光性质。由1-（3'-脱氧吡喃呋喃糖基）尿嘧啶5 [ ]合成了关键中间体，其是通过吩嗪呋喃糖基尿嘧啶衍生物7和8与吩嗪1'连接的，该连接基由磷酸酯和两个亚甲基组成。化合物7转化成相应的6'- ø -DMTr保护的4'-亚磷酰胺块13中的三个步骤[7→9（83％）→11（83％）→13（83％）]，而化合物8在四个步骤[8→10（28％）→12（70％）→14 ]中，使用α-己内酰胺来制备改性的固体载体14。改性的9-mer寡核苷酸28 - 31和18-mer的寡核苷酸22 - 25然后在使用自动固相DNA合成协议通常的方式组装。吩嗪-拴系的九聚体（28 - 31），用于它们的能力，形成稳定的双链体与靶DNA-链（测试19 - 20）。测试了吩嗪系留的18聚体（22
• The PdCl2/R3SiH system for the silylation of nucleosides
  作者：Carla Ferreri、Cristina Costantino、Roberto Romeo、Chryssostomos Chatgilialoglu

  DOI：10.1016/s0040-4039(98)02564-7

  日期：1999.2

  Convenient syntheses of TIPDS-Cl-2, and TBDMS-Br from the corresponding hydrides were obtained by using catalytic PdCl2 and CCl4 or CH2Br2, respectively. These systems can be successfully applied in tandem procedures for improved silylation Of nucleosides. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Phosphono Nucleoside. 2. Synthesis of 1'-Deoxy-1'-phosphono-1-b-D-fructofuranosyluracil and 1',3'-Dideoxy-1'-phosphono-1-b-D-fructofuranosyluracil
  作者：Toshio Tatsuoka、Kayoko Imao、Kenji Suzuki

  DOI：10.3987/r-1986-08-2133

  日期：——
• Independent Generation and Reactivity of 2‘-Deoxyurid-1‘-yl
  作者：Brian K. Goodman、Marc M. Greenberg

  DOI：10.1021/jo951769a

  日期：1996.1.1
• C1′ Acylated Derivatives of 2′-Deoxyuridine. Photolabile Precursors of 2′-Deoxyuridin-1′-yl
  作者：Marc M. Greenberg、Dong Jin Yoo、Brian K. Goodman

  DOI：10.1080/07328319708002519

  日期：1997.1

  C1' acylated derivatives of 2'-deoxyuridine (1a-c) were synthesized from 1-[3-deoxy-beta-D-psicofuranosyl]uracil (6). The acyl group is introduced via the C1' aldehyde (11). Following nucleophilic addition, the ketones (1a-c) are obtained via periodinane oxidation and desilylation with NH4F.