2',3'-O-cyclohexylidene-5-methyluridine 5'-aldehyde | 1191255-80-7

• 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: 2',3'-O-cyclohexylidene-5-methyluridine 5'-aldehyde
• CAS: 1191255-80-7
• 化学式: C₁₆H₂₀N₂O₆
• 分子量: 336.345
• InChiKey: DYBXSNOAQAWOTC-HKUMRIAESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.39
• 重原子数：
  24.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  99.62
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2',3'-O-cyclohexylidene-5-methyluridine 5'-aldehyde 在 咪唑 、 sodium hydroxide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 85.0h， 生成 1-((3a′S,4′R,6′R,6a′R)-4′-(((tert-butyldiphenylsilyl)oxy)methyl)-4′-(hydroxymethyl)tetrahydrospiro[cyclohexane-1,2′-furo[3,4-d][1,3]-dioxol]-6′-yl)-5-methylpyrimidine-2,4-(1H,3H)-dione
  参考文献：
  名称：

  Alternative Syntheses of (S)-cEt-BNA: A Key Constrained Nucleoside Component of Bioactive Antisense Gapmer Sequences

  摘要：

  Approaches to the synthesis of the constrained 5-methyluracil nucleoside (S)-cEt-BNA, a key "gapmer" unit in a number of biologically relevant antisense oligonucleotides, are described using 5-methyluridine as starting material. In the shorter synthesis, a nine-step linear sequence afforded a O-protected (S)-cEt-BNA consisting of a [2.2.1]dioxabicycloheptane core in 7% overall yield. A competing reaction in an intramolecular cyclization of a tosylate led to a bicyclic oxetane.

  DOI：

  10.1021/jo502320y
• 作为产物：
  描述：

  5-甲基尿甙 在 camphor-10-sulfonic acid 、 碳酸氢钠 、 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 5.0h， 生成 2',3'-O-cyclohexylidene-5-methyluridine 5'-aldehyde
  参考文献：
  名称：

  Alternative Syntheses of (S)-cEt-BNA: A Key Constrained Nucleoside Component of Bioactive Antisense Gapmer Sequences

  摘要：

  Approaches to the synthesis of the constrained 5-methyluracil nucleoside (S)-cEt-BNA, a key "gapmer" unit in a number of biologically relevant antisense oligonucleotides, are described using 5-methyluridine as starting material. In the shorter synthesis, a nine-step linear sequence afforded a O-protected (S)-cEt-BNA consisting of a [2.2.1]dioxabicycloheptane core in 7% overall yield. A competing reaction in an intramolecular cyclization of a tosylate led to a bicyclic oxetane.

  DOI：

  10.1021/jo502320y

文献信息

• PROCESS FOR PRODUCTION OF ETHYNYLTHYMIDINE COMPOUND USING 5-METHYLURIDINE AS STARTING RAW MATERIAL
  申请人：Hamari Chemicals, Ltd.

  公开号：EP2277878B1

  公开（公告）日：2014-09-17
• Alternative Syntheses of (<i>S</i>)-cEt-BNA: A Key Constrained Nucleoside Component of Bioactive Antisense Gapmer Sequences
  作者：Juan C. Salinas、Michael T. Migawa、Bradley L. Merner、Stephen Hanessian

  DOI：10.1021/jo502320y

  日期：2014.12.5

  Approaches to the synthesis of the constrained 5-methyluracil nucleoside (S)-cEt-BNA, a key "gapmer" unit in a number of biologically relevant antisense oligonucleotides, are described using 5-methyluridine as starting material. In the shorter synthesis, a nine-step linear sequence afforded a O-protected (S)-cEt-BNA consisting of a [2.2.1]dioxabicycloheptane core in 7% overall yield. A competing reaction in an intramolecular cyclization of a tosylate led to a bicyclic oxetane.