O^3'-(1-isopropyl-silolan-1-yl)-thymidine | 54925-54-1

• 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: O^3'-(1-isopropyl-silolan-1-yl)-thymidine
• CAS: 54925-54-1
• 化学式: C₁₇H₂₈N₂O₅Si
• 分子量: 368.505
• InChiKey: DTEJAHMVOIWQRM-RRFJBIMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.66
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  93.55
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 O^3'-(1-isopropyl-silolan-1-yl)-thymidine 以 吡啶 为溶剂， 生成 Acetic acid (2R,3S,5R)-3-(1-isopropyl-silolan-1-yloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester
  参考文献：
  名称：

  Mass spectrometry of trialkylsilyl and acyl derivatives of 2′-deoxynucleosides

  摘要：

  AbstractThe electron impact mass spectra of monosilyl and mixed acyl‐silyl derivatives of 2′‐deoxynucleosides are described in detail. (Silyl = tert‐butyldimethylsilyl, cyclo‐tetramethylene‐isopropylsilyl, or cyclo‐tetramethylene‐tert‐butylsilyl; acyl = acetyl or trifluoroacetyl.) The interpretation of the fragmentation pathways was aided by metastable ion decomposition studies, precise mass and deuterium labelling measurements. Mass spectrally, the acyl substituents are mostly ‘passive’ and have (with possibly one exception) little fragmentation directing capability. In contrast, the silyl groups have powerful fragmentation directing properties. Elimination of the bulky alkyl radical R˙ (tert‐butyl or isopropyl) from the molecular ion produces the siliconium ion, [M–R]+, which is the precursor for most of the other prominent ions in the spectra. These arise from ‘siliconium ion rearrangements’ resulting from the interaction of the positively charged siliconium ion centre with the electron dense regions (i.e. oxygens) in the molecule, to form cyclic silyloxonium ions which subsequently decompose. Since the interacting oxygen and silicon must be sterically accessible, the fragment ion types and their abundances are very dependent upon structure. Consequently, [M–R]+ ions formed from 3′‐ or 5′‐O‐silyl groups give rise to different sets of daughter ions which, for the most part, are not found, or have very low abundances, in the mass spectra of underivatized or trimethylsilylated nucleosides. Detailed information on sugar and base moieties and isomeric substitution is readily obtained.

  DOI：

  10.1002/oms.1210160307
• 作为产物：
  描述：

  Cyclo-tetramethylen-iso-propyl-chlor-silan 、 beta-胸苷 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 O^3'-(1-isopropyl-silolan-1-yl)-thymidine 、 O5'-(1-isopropyl-silolan-1-yl)-thymidine
  参考文献：
  名称：

  Ogilvie; Beaucage; Entwistle, Journal of Carbohydrates Nucleosides Nucleotides, 1976, vol. 3, # 4, p. 197 - 227

  摘要：

  DOI：