4-N-Acetyl-2',3',5'-tri-O-benzoylcytidin | 27391-03-3

• 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: 4-N-Acetyl-2',3',5'-tri-O-benzoylcytidin
• 英文别名: N⁴-acetyl-O^2'_,O3'_,O5'-tribenzoyl-cytidine；N⁴-Acetyl-O^2'_,O3'_,O5'-tribenzoyl-cytidin；[(2R,3R,4R,5R)-5-(4-acetamido-2-oxopyrimidin-1-yl)-3,4-dibenzoyloxyoxolan-2-yl]methyl benzoate
• CAS: 27391-03-3
• 化学式: C₃₂H₂₇N₃O₉
• 分子量: 597.581
• InChiKey: MZQCGCNOHZFRNR-YULOIDQLSA-N

物化性质

• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  44
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  150
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  4-N-Acetyl-2',3',5'-tri-O-benzoylcytidin 在 乙醇 、 氨 作用下， 生成 胞苷
  参考文献：
  名称：

  Pyrimidine Nucleosides. III. On the Syntheses of Cytidine and Related Pyrimidine Nucleosides¹

  摘要：

  DOI：

  10.1021/ja01575a063
• 作为产物：
  描述：

  N⁴-acetyl-O-trimethylsilylcytosine 、 2,3,5-tri-O-benzoyl-d-ribofuranosyl iodide 以 乙腈 为溶剂， 生成 4-N-Acetyl-2',3',5'-tri-O-benzoylcytidin
  参考文献：
  名称：

  Glycosyl iodides. History and recent advances

  摘要：

  The use of glycosyl iodides as an effective method for the preparation of glycosides has had a recent resurgence in carbohydrate chemistry, despite its early roots in which these species were believed to be of limited use. Renewed interest in these species as glycosylating agents has been spurred by their demonstrated utility in the stereoselective preparation of O-glycosides, and other glycosylic compounds. This review provides a brief historical account followed by an examination of the use of glycosyl iodides in the synthesis of oligosaccharicles and other glycomimetics, including C-glycosylic compounds, glycosyl azides and N-glycosides. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.02.032

文献信息

• Chemoselective<i>N-</i>Deacetylation of Protected Nucleosides and Nucleotides Promoted by Schwartz's Reagent
  作者：Valentina Ferrari、Michaela Serpi、Christopher McGuigan、Fabrizio Pertusati

  DOI：10.1080/15257770.2015.1075552

  日期：2015.11.2

  deprotection strategies involving the N-acetyl group are widely utilized in nucleoside and nucleotide chemistry. Herein, we present a mild and selective N-deacetylation methodology, applicable to purine and pyrimidine nucleosides, by means of Schwartz's reagent, compatible with most of the common protecting groups used in nucleoside chemistry.

  涉及N-乙酰基的保护和脱保护策略被广泛用于核苷和核苷酸化学中。在本文中，我们提出了一种温和的选择性N-脱乙酰化方法，该方法可通过Schwartz试剂与嘌呤和嘧啶核苷一起使用，与核苷化学中使用的大多数常见保护基团兼容。