4-(tetrazol-1-yl)-1-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)pyrimidin-2(1H)-one | 76991-96-3

• 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-(tetrazol-1-yl)-1-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)pyrimidin-2(1H)-one
• 英文别名: [(2R,3R,4R,5R)-3,4-diacetyloxy-5-[2-oxo-4-(tetrazol-1-yl)pyrimidin-1-yl]oxolan-2-yl]methyl acetate
• CAS: 76991-96-3
• 化学式: C₁₆H₁₈N₆O₈
• 分子量: 422.354
• InChiKey: PSVAUUIGQYVOMR-NMFUWQPSSA-N

物化性质

• 沸点：
  603.1±65.0 °C(Predicted)
• 密度：
  1?+-.0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  164
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  4-(tetrazol-1-yl)-1-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)pyrimidin-2(1H)-one 在 TEA 、 乙酸酐 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 37.0h， 生成 2',3',5'-tri-O-acetyl-N4-succinylcytidine
  参考文献：
  名称：

  对于[4-合成的有效方法，15 N]胞苷和[6- 15 N]从尿苷和肌苷腺苷衍生物

  摘要：

  由尿苷和肌苷转化的4-偶氮基-1-β-D-呋喃核糖基嘧啶-2（1H）-一和6-偶氮基-9-β-D-呋喃核糖基-9H-嘌呤衍生物的亲核取代反应与[ 15在三乙胺或DBU存在N]邻苯二甲酰亚胺被发现，得到[4- 15 N] - ñ 4 -phthaloylcytidine和[6- 15 N] - ñ 6个分别-phthaloyladenosine衍生物，以高收率，而与琥珀酰亚胺反应还以高收率得到了N 4-琥珀酰胞苷和N 6-琥珀酰腺苷衍生物。

  DOI：

  10.1016/0040-4039(94)02173-9
• 作为产物：
  描述：

  2',3',5'-三乙酰尿苷 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 1,4-二氧六环 、 吡啶 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 4-(tetrazol-1-yl)-1-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)pyrimidin-2(1H)-one
  参考文献：
  名称：

  Structural assignment of n3-acylated uridine derivatives by means of 13c nmr spectroscopy

  摘要：

  DOI：

  10.1016/s0040-4039(01)81406-4

文献信息

• An Efficient Method for the Synthesis of [4–¹⁵N]Cytidine, 2′-Deoxy[4–¹⁵N]Cytidine, [6–¹⁵N]adenosine, and 2′-Deoxy [6–¹⁵N]adenosine Derivatives
  作者：Kazuo Kamaike、Mihoko Takahashi、Kazuyuki Utsugi、Kazue Tomizuka、Yasunori Okazaki、Yuri Tamada、Kazutomo Kinoshita、Hiroyuki Masuda、Yoshiharu Ishido

  DOI：10.1080/07328319608002421

  日期：1996.1

  Nucleophilic substitution reactions of 4-azolyl-1-beta-D-ribofuranosyl-pyrimidin-2(1H)-one and 6-azolyl-9-beta-D-ribofuranosyl-9H-purine derivatives, which were converted from uridine and inosine, with [N-15]phthalimide in the presence of triethylamine or DBU gave N-4-phthaloyl[4-N-15]cytidine and N-6-phthaloyl[6-N-15]- adenosine derivatives, respectively, in high yields. Similar reactions of those azolyl derivatives with succinimide afforded N-4-succinylcytidine and N-6-succinyladenosine derivatives in high yields. The corresponding 2'-deoxyribonucleosides were also synthesized efficiently through the same procedure.
• Synthesis and solution conformation studies of the modified nucleoside N4,2′-O-dimethylcytidine (m4Cm) and its analogues
  作者：Santosh K. Mahto、Christine S. Chow

  DOI：10.1016/j.bmc.2008.09.016

  日期：2008.10

  The dimethylated ribosomal nucleoside m(4)Cm and its monomethylated analogues Cm and m(4)C were synthesized. The conformations (syn vs anti) of the three modified nucleosides and cytidine were determined by CD and 1D NOE difference spectroscopy. The ribose sugar puckers were determined by the use of proton coupling constants. The position of modi. cation (e. g., O vs N methylation) was found to have an effect on the sugar pucker of cytidine. (C) 2008 Elsevier Ltd. All rights reserved.
• High-Yielding Preparation of [3-¹⁵N]Cytidine, [4-¹⁵NH₂]Cytidine, and [3-¹⁵N,4-¹⁵NH₂]Cytidine
  作者：Xavier Ariza、Jaume Vilarrasa

  DOI：10.1021/jo9918706

  日期：2000.5.1