2'-deoxy-3'-O,4-N-diacetylcytidine | 70284-47-8

• 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: 2'-deoxy-3'-O,4-N-diacetylcytidine
• 英文别名: 2'-deoxy-3'-O,N⁴-diacetylcytidine；4-N,3'-O-diacetyl-2'-deoxycytidine；N⁴-acetyl-1-<3'-O-acetyl-2'-deoxy-β-D-arabinofuranosyl>cytosine；N⁴,O^3'-diacetyl-2'-deoxy-cytidine；N⁴,O^3'-Diacetyl-2'-desoxy-cytidin；[(2R,3S,5R)-5-(4-acetamido-2-oxopyrimidin-1-yl)-2-(hydroxymethyl)oxolan-3-yl] acetate
• CAS: 70284-47-8
• 化学式: C₁₃H₁₇N₃O₆
• 分子量: 311.294
• InChiKey: URRCDYLSABOZNS-HOSYDEDBSA-N

物化性质

• 密度：
  1.51±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  118
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2'-deoxy-3'-O,4-N-diacetylcytidine 在 吡啶 、 乙醇 、 水 、 钯 作用下， 生成 2'-脱氧胞苷-5'-单磷酸
  参考文献：
  名称：

  核苷酸。第二十三部分。衍生自脱氧胞苷的单核苷酸。注意胞苷酸a和b的结构

  摘要：

  DOI：

  10.1039/jr9540000034
• 作为产物：
  描述：

  N-乙酰基-5'-O-(4,4'-二甲氧基三苯甲基)-2'-脱氧胞苷 在 二氯乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 生成 2'-deoxy-3'-O,4-N-diacetylcytidine
  参考文献：
  名称：

  Differential reactivity of carbohydrate hydroxyls in glycosylations. II. The likely role of intramolecular hydrogen bonding on glycosylation reactions. Galactosylation of nucleoside 5′-hydroxyls for the syntheses of novel potential anticancer agents

  摘要：

  与预期相反，许多主要的羟基在糖基化反应中完全不活跃，或者以非常低的产率给出所需的糖苷，伴随着许多副反应产物。这些主要羟基的氢被显示为分子内氢键结合。由这些羟基对活化的糖基化试剂的亲核攻击形成的中间体可能会抵抗氢的提取。据推测，这种抵抗质子损失的现象是观察到的不活性的起源。研究表明，成功的糖基化反应发生在酸性条件下，这种条件下这种氢键不再存在。因此，首次利用三氯乙酰亚胺盐酸镓在氯仿中在三氟乙酸银的促进下，成功地对核苷的通常不活跃的5'-羟基进行了直接的半乳糖化。据指出，这种半乳糖化的抗癌核苷可能具有改善的生物特异性。

  DOI：

  10.1139/v94-284

文献信息

• 5′-Phosphonates of Ribonucleosides and 2′-Deoxyribonucleosides: Synthesis and Antiviral Activity
  作者：Maxim Jasko、Alexander Shipitsin、Elena Shirokova、Alexander Krayevsky、Bruce Polsky、Penny Baron、Clarinda MacLow、Michael Ostrander、Brian O'Hara

  DOI：10.1080/07328319308018558

  日期：1993.9

  5'-Phosphonates of natural 2'-deoxynucleosides and ribonucleosides were synthesized by condensation of 3'-O-acylated 2'-deoxynucleosides or 2',3'-substituted (2',3'-O-isopropylidene, 2',3'-O-methoxymethylene or 2',3'-O-ethoxymethylene) ribonucleosides. As condensing agents, either N,N'-dicyclohexylcarbodiimide or 2,4,6-triisopropylbenzenesulphonyl chloride were used. Nucleoside 5'-ethoxycarbonylphosphonates were converted into corresponding nucleoside 5'-aminocarbonylphosphonates by action of ammonia in methanol or aqueous ammonia. 5'-Hydrogenphosphonothioates of thymidine and 3'-deoxythymidine were obtained by reaction of phosphinic acid in the presence of pivaloyl chloride with 3'-O-acetylthymidine or 3'-deoxythymidine, respectively, followed by addition of powedered sulfur. 5'-O-methylenephosphonates of thymidine and 2'-deoxyadenosine were prepared by intramolecular reaction of corresponding 3'-O-iodomethylphosphonates under basic conditions. All compounds were tested for inhibition of several viruses, including HSV-2 and CMV, but showed no activity. A few compounds insignificantly inhibited HIV-1 reproduction. Thymidine 5'-hydrogenphosphonate neutralized anti-HIV action of 3'-azido-3'-deoxythymidine (AZT) and it indirectly showed that even some nucleoside 5'-phosphonates could be partly hydrolyzed in cell culture to corresponding nucleosides.
• Synthesis and characterization of oligonucleotide peptides
  作者：James K. Bashkin、Randy J. McBeath、Anil S. Modak、Kirby R. Sample、William B. Wise

  DOI：10.1021/jo00009a044

  日期：1991.4

  The transport and reactivity of oligonucleotides may be altered by attaching pendant peptides, and it is of interest to develop general synthetic methods for such bioconjugates. Two protecting group strategies are described for the synthesis of nucleotide peptides containing a lysine residue. The preparation of a lysine-nucleopeptide phosphoramidite reagent is described, along with its use in solid-phase DNA synthesis. Di- and trinucleotides were prepared with pendant and extensively characterized by NMR. These studies showed the peptide side chains to have survived DNA synthesis conditions; we then incorporated nucleopeptide residues into longer oligonucleotides. A similar approach is described for the preparation of oligonucleotide histidines. Previously reported histidine-nucleopeptides serve as precursors to phosphoramidites and to phosphodiester DNA building blocks. Both solution- and solid-phase techniques are presented for the preparation of histidine-containing oligonucleotides. The methodology developed here allows the incorporation of nucleopeptide residues at internal positions in a DNA sequence, using standard reagents. We present a complete description of the synthesis, purification, and characterization (via mass spectral and NMR methods) of the novel compounds.
• Conformational transmission in nucleotides containing trigonal bipyramidal phosphorus as the internucleoside linkage
  作者：Leo H. Koole、Marcel H. P. Van Genderen、Henk M. Buck

  DOI：10.1021/jo00257a012

  日期：1988.10
• Andersen et al., Journal of the Chemical Society, 1954, p. 1882,1884
  作者：Andersen et al.

  DOI：——

  日期：——
• BASHKIN, JAMES K.;MCBEATH, RANDY J.;MODAK, ANIL S.;SAMPLE, KIRBY R.;WISE,+, J. ORG. CHEM., 56,(1991) N, C. 3168-3176
  作者：BASHKIN, JAMES K.、MCBEATH, RANDY J.、MODAK, ANIL S.、SAMPLE, KIRBY R.、WISE,+

  DOI：——

  日期：——