1-(2-Deoxy-3,5-di-O-acetyl-β-D-ribofuranosyl)-4-chloro-5-methyl-2(1H)-pyrimidinone | 91290-54-9

• 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: 1-(2-Deoxy-3,5-di-O-acetyl-β-D-ribofuranosyl)-4-chloro-5-methyl-2(1H)-pyrimidinone
• 英文别名: 3',5'-di-O-acetyl-4-chlorothymidine；[(2R,3S,5R)-3-acetyloxy-5-(4-chloro-5-methyl-2-oxopyrimidin-1-yl)oxolan-2-yl]methyl acetate
• CAS: 91290-54-9
• 化学式: C₁₄H₁₇ClN₂O₆
• 分子量: 344.752
• InChiKey: RJJNFEWFGQPGTQ-QJPTWQEYSA-N

物化性质

• 沸点：
  450.6±55.0 °C(Predicted)
• 密度：
  1.47±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  94.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(2-Deoxy-3,5-di-O-acetyl-β-D-ribofuranosyl)-4-chloro-5-methyl-2(1H)-pyrimidinone 在 ammonium hydroxide 、 三乙胺 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 39.0h， 生成 1-(2-deoxy-β-D-erythro-pentofuranosyl)-4-<(carboxymethyl)amino>-5-methylpyrimidin-2(1H)-one
  参考文献：
  名称：

  嘧啶核苷的新衍生物：合成，理化性质和生物活性

  摘要：

  本文报道了八个新的嘧啶核苷C-4取代的和两个咪唑并[1,2- c ]嘧啶核苷的合成和理化数据，以及它们对培养的神经母细胞瘤细胞的生物学作用的初步结果。

  DOI：

  10.1002/jhet.5570250365
• 作为产物：
  描述：

  3,5-双-O-乙酰胸苷 在 1H-1,2,3-三氮唑 、 三氯氧磷 作用下， 以 吡啶 为溶剂， 反应 4.0h， 生成 1-(2-Deoxy-3,5-di-O-acetyl-β-D-ribofuranosyl)-4-chloro-5-methyl-2(1H)-pyrimidinone
  参考文献：
  名称：

  Unexpected Shift to a 4-Imino Tautomer Upon N⁴-Acylation of 5-Methylcytosin-1-yl Nucleoside Analogues

  摘要：

  In contrast with the behaviour of 5-unsubstituted cytosine nucleoside analogues, 5-methylcytosine derivatives show upon N-4-benzoylation, commonly used as base protection in oligonucleotide synthesis, a tautomeric change of the base moiety from a 4-amino- into a 4-imino isomer. In the latter form, which is easily diagnosticized by C-13 NMR and confirmed by X-ray data, the compounds seem to be hydrolytically less stable.

  DOI：

  10.1080/15257779908041652

文献信息

• Synthesis of novel pyrimidine nucleoside analogues
  作者：Lorenzo De Napoli、Luciano Mayol、Gennaro Piccialli、Mosé Rossi、Ciro Santacroce

  DOI：10.1002/jhet.5570230529

  日期：1986.9

  Two new tetrazolopyrimidinedeoxynucleosides were synthesized and their physico-chemical data are described. Results of preliminary analyses of their biological properties are also reported.

  合成了两种新的四唑并嘧啶脱氧核苷，并描述了它们的理化数据。还报告了对其生物学特性的初步分析结果。
• Mayol, Luciano; Piccialli, Gennardo; Rossi, Mose, Gazzetta Chimica Italiana, 1983, vol. 113, # 11/12, p. 863 - 864
  作者：Mayol, Luciano、Piccialli, Gennardo、Rossi, Mose、Santacroce, Ciro

  DOI：——

  日期：——
• Reactions of Pd(PPh₃)₄ with 3‘,5‘-Di-<i>O</i>-acetylthymidine:  Oxidative Addition of Pd(PPh₃)₄ on Thymidine N3 and C4 Atoms
  作者：Alessandra Romanelli、Rosa Iacovino、Gennaro Piccialli、Francesco Ruffo、Lorenzo De Napoli、Carlo Pedone、Benedetto Di Blasio、Anna Messere

  DOI：10.1021/om050058s

  日期：2005.7.1

  Oxidative addition reactions of Pd(PPh3)(4) on the pyrimidine nucleosides 3',5'-di-O-acetylthymidine and 3',5'-di-O-acetyl-4-chlorothymidine and on the nucleobase 1-methylthymine have been investigated. N3 and C4 metal coordinated complexes 3 and 7 wend isolated and characterized by spectroscopic techniques. Moreover, the crystal structur, of the trans[PdCl(l-methyl thymine)(PPh3)(2)]center dot H2O (4) is reported.
• BARBATO, STEFANIA;PICCIALLI, GENNARO;SANTACROCE, CIRO, NUCLEOSIDES AND NUCLEOTIDES, 8,(1989) N, C. 515-528
  作者：BARBATO, STEFANIA、PICCIALLI, GENNARO、SANTACROCE, CIRO

  DOI：——

  日期：——
• BARBATO, STEFANIA;PICCIALLI, GENNARO;SANTACROCE, CIRO;DE, NAPOLI LORENZO;+, NUCLEOSIDES AND NUCLEOTIDES, 10,(1991) N, C. 853-866
  作者：BARBATO, STEFANIA、PICCIALLI, GENNARO、SANTACROCE, CIRO、DE, NAPOLI LORENZO、+

  DOI：——

  日期：——