3',5'-O-bis(triisopropylsilyl)-2'-deoxycytidine | 109460-88-0

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 3',5'-O-bis(triisopropylsilyl)-2'-deoxycytidine
• 英文别名: 2'-Deoxy-3',5'-bis(triisopropylsilyl)cytidine；2'-deoxy-3',5'-di-O-triisopropylsilylcytidine；3,5-bis(triisopropylsilyl)-2-deoxycytosine；di-O-triisopropylsilyl-2'-deoxycytidine；4-amino-1-[(2R,4S,5R)-4-tri(propan-2-yl)silyloxy-5-[tri(propan-2-yl)silyloxymethyl]oxolan-2-yl]pyrimidin-2-one
• CAS: 109460-88-0
• 化学式: C₂₇H₅₃N₃O₄Si₂
• 分子量: 539.907
• InChiKey: ZHUHCNOSICSKPZ-BFLUCZKCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.87
• 重原子数：
  36
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  86.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  triphenylphosphine-cyanoborane 、 3',5'-O-bis(triisopropylsilyl)-2'-deoxycytidine 以 四氢呋喃 为溶剂， 以46%的产率得到
  参考文献：
  名称：

  含硼核酸。2'-脱氧核苷的氰基硼烷加合物的合成

  摘要：

  2'-脱氧核苷的氰硼烷加合物，特别是 2'-脱氧鸟苷-N7-氰基硼烷、2'-脱氧腺苷-N1-氰基硼烷、2'-脱氧肌苷-N7-氰基硼烷和 2'-脱氧胞苷-N3-氰基硼烷，由三苯基膦-氰基硼烷 (Ph 3 PBH 2 CH) 与 3',5'-O-保护的核苷的交换反应

  DOI：

  10.1021/ja00208a019
• 作为产物：
  描述：

  三异丙基氯硅烷 、 2'-脱氧胞嘧啶核苷 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以36%的产率得到3',5'-O-bis(triisopropylsilyl)-2'-deoxycytidine
  参考文献：
  名称：

  汇聚的官能团XI。鸟苷衍生物的选择性结合。

  摘要：

  引入了鸟苷衍生物的新的合成受体，并使用溶解度滴定法进行了评估。在CDCl 3中观察到碱基配对和一些芳香族堆积效应。

  DOI：

  10.1016/s0040-4020(01)81785-3

文献信息

• Convergent functional groups XI. Selective binding of guanosine derivatives.
  作者：Tae Kyo Park、Joseph Schroeder、Julius Rebek

  DOI：10.1016/s0040-4020(01)81785-3

  日期：1991.1

  New synthetic receptors for guanosine derivatives are introduced and evaluated using solubility titration methods. Base-pairing and some aromatic stacking effects are observed in CDCl3.

  引入了鸟苷衍生物的新的合成受体，并使用溶解度滴定法进行了评估。在CDCl 3中观察到碱基配对和一些芳香族堆积效应。
• Vibrational analysis of the hydrogen bonding of cytidine and guanosine derivatives
  作者：Pedro Carmona、Marina Molina、Aurora Lasagabaster、Rosario Escobar、Aida Ben Altabef

  DOI：10.1021/j100139a042

  日期：1993.9

  Hydrogen bonding between 2'-deoxy-3',5'-bis(triisopropylsilyl)guanosine (G) and 2'-deoxy-3',5'-bis(triisopropylsilyl) cytidine (C) has been studied by vibrational spectroscopy in chloroform solution. Strong interactions occur between the two derivatives of guanosine and cytidine and between CG base pair and cytidine, whose association constants were first determined. CGC trimers involve cyclic hydrogen bonds through the N(3) acceptors of both nucleobases and the guanine N(2)H and cytosine N(4)H donors. The main spectral changes of CG dimer accompanying CGC trimer formation are intensity and frequency decreases of the Raman band of guanine base near 1570 cm-1 as well as downshifting of the 1534-cm-1 Raman band of the cytosine base that binds to the previously formed CG base pair. Similar spectral changes are observed for the infrared bands located near these frequencies. The 1483-cm-1 band of guanine is sensitive to hydrogen bonding at the N(7) position. Since this band is unchanged when the CG dimer is converted to the CGC trimer, it is concluded that no binding at the G(7) position occurs in the trimer. Raman spectroscopy can, then, distinguish between hydrogen bonds involving guanine N(7) and N(3) acceptors and offers prospect for determining these specific interactions in polynucleotide triplexes and nucleic acid-protein recognition.
• Boron-containing nucleic acids. Synthesis of cyanoborane adducts of 2'-deoxynucleosides
  作者：Anup Sood、Barbara Ramsay Shaw、Bernard F. Spielvogel

  DOI：10.1021/ja00208a019

  日期：1989.12

  Cyanoborane adducts of 2'-deoxynucleosides, specifically 2'-deoxyguanosine-N7-cyanoborane, 2'-deoxyadenosine-N1-cyanoborane, 2'-deoxyinosine-N7-cyanoborane, and 2'-deoxycytidine-N3-cyanoborane, were prepared by an exchange reaction of triphenylphosphine-cyanoborane (Ph 3 PBH 2 CH) with 3',5'-O-protected nucleosides

  2'-脱氧核苷的氰硼烷加合物，特别是 2'-脱氧鸟苷-N7-氰基硼烷、2'-脱氧腺苷-N1-氰基硼烷、2'-脱氧肌苷-N7-氰基硼烷和 2'-脱氧胞苷-N3-氰基硼烷，由三苯基膦-氰基硼烷 (Ph 3 PBH 2 CH) 与 3',5'-O-保护的核苷的交换反应