methyl 5-deoxy-5-(2,4-dioxopyrimidin-1H-1-yl)-2,3-O-isopropylidene-β-D-ribofuranoside | 55221-59-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: methyl 5-deoxy-5-(2,4-dioxopyrimidin-1H-1-yl)-2,3-O-isopropylidene-β-D-ribofuranoside
• 英文别名: 1-[[(3aR,4R,6R,6aR)-4-methoxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methyl]pyrimidine-2,4-dione
• CAS: 55221-59-5
• 化学式: C₁₃H₁₈N₂O₆
• 分子量: 298.296
• InChiKey: BZELZZMOPOKRAQ-QCNRFFRDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  86.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 5-deoxy-5-(2,4-dioxopyrimidin-1H-1-yl)-2,3-O-isopropylidene-β-D-ribofuranoside 在 盐酸 作用下， 以86%的产率得到
  参考文献：
  名称：

  Synthesis of "Reversed" and "Double Headed" Nucleosides

  摘要：

  The synthesis of several partially and fully deprotected ''reversed'' nucleosides are described starting from ''reversed'' 5-iodouracil-1-yl nucleoside 1. The preparation of a novel purine-purine and mixed purine-pyrimidine ''double headed'' nucleosides via ''reversed'' purine nucleoside 12 is also described.

  DOI：

  10.1080/15257779508012377
• 作为产物：
  描述：

  甲基-2,3-O-异亚丙基-beta-D-呋喃核糖苷 在 吡啶 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 21.5h， 生成 methyl 5-deoxy-5-(2,4-dioxopyrimidin-1H-1-yl)-2,3-O-isopropylidene-β-D-ribofuranoside
  参考文献：
  名称：

  Synthesis and Biological Activity of Reversed Pyrimidine Nucleosides

  摘要：

  An efficient approach to reversed nucleosides which enables their synthesis in gram quantities is described. N-1'-Pyrimidine reversed nucleosides were prepared by treating of the sodium salt of pyrimidine bases with protected 5-tosyl ribose. Additionally, N-1',N-3'-disubstituted reversed nucleosides were isolated in the condensation reactions with the 5-halogen pyrimidines. Using the Sonogashira coupling of 5'-iodouracil reversed nucleoside with ethynyltrimethyl silane gave 5'-ethynyl derivative which was further transformed into 5'-acetyl reversed nucleoside. Biological activity of deprotected reversed nucleosides was validated on the panel of six human carcinoma cell lines (HeLa, MIAPaCa2, Hep2, NCI-H358, CaCo-2, and HT-29). 5'-Iodouracil derivative displayed moderate growth inhibition activity against human colon carcinoma (CaCo-2) cells.

  DOI：

  10.5562/cca2531

文献信息

• A novel synthesis of “double headed” nucleosides “reversed” nucleosides
  作者：Biserka Kašnar、Vinko Škarić、Branimir Klaić、Mladen Žinić

  DOI：10.1016/s0040-4039(00)74067-6

  日期：1993.7

  The ''double headed' nucleosides 10, 11 and 13 bearing pyrimidine or purine bases attached on C-1 and C-5 positions of single ribose unit have been synthesized following a new synthetic strategy. The strategy rests on the introduction of the first nucleo base at C-5 position of the ribose unit giving 'reversed' nucleoside and the subsequent attachment of the second base at C-1 position of the ribose, by classical glycosylation reaction. This order of the base attachments gave much better yields on the ''double headed' nucleosides then previously known C-1 then C-5 order of attachments.
• Synthesis and Biological Activity of Reversed Pyrimidine Nucleosides
  作者：Nataša Župančić、Željka Ban、Josipa Matić、Dijana Saftić、Ljubica Glavaš-Obrovac、Biserka Žinić

  DOI：10.5562/cca2531

  日期：——

  An efficient approach to reversed nucleosides which enables their synthesis in gram quantities is described. N-1'-Pyrimidine reversed nucleosides were prepared by treating of the sodium salt of pyrimidine bases with protected 5-tosyl ribose. Additionally, N-1',N-3'-disubstituted reversed nucleosides were isolated in the condensation reactions with the 5-halogen pyrimidines. Using the Sonogashira coupling of 5'-iodouracil reversed nucleoside with ethynyltrimethyl silane gave 5'-ethynyl derivative which was further transformed into 5'-acetyl reversed nucleoside. Biological activity of deprotected reversed nucleosides was validated on the panel of six human carcinoma cell lines (HeLa, MIAPaCa2, Hep2, NCI-H358, CaCo-2, and HT-29). 5'-Iodouracil derivative displayed moderate growth inhibition activity against human colon carcinoma (CaCo-2) cells.
• Synthesis of "Reversed" and "Double Headed" Nucleosides
  作者：B. Kasnar

  DOI：10.1080/15257779508012377

  日期：1995.5.1

  The synthesis of several partially and fully deprotected ''reversed'' nucleosides are described starting from ''reversed'' 5-iodouracil-1-yl nucleoside 1. The preparation of a novel purine-purine and mixed purine-pyrimidine ''double headed'' nucleosides via ''reversed'' purine nucleoside 12 is also described.