Acetic acid (2R,3R,4S,5R,6R)-3-acetoxy-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-6-hydroxy-1-oxa-spiro[4.4]non-4-yl ester | 385827-51-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid (2R,3R,4S,5R,6R)-3-acetoxy-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-6-hydroxy-1-oxa-spiro[4.4]non-4-yl ester
• CAS: 385827-51-0
• 化学式: C₁₆H₂₀N₂O₈
• 分子量: 368.343
• InChiKey: DEJHLYRVHITRKV-RSQMQNDGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.79
• 重原子数：
  26.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  136.92
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3R,4S,5R,6R)-3-acetoxy-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-6-hydroxy-1-oxa-spiro[4.4]non-4-yl ester 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 以99%的产率得到1-((2R,3R,4S,5R,6R)-3,4,6-Trihydroxy-1-oxa-spiro[4.4]non-2-yl)-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Spirocyclic Restriction of Nucleosides. An Analysis of Protecting Group Feasibility while Accessing Prototype anti-1-Oxaspiro[4.4]nonanyl Mimics

  摘要：

  [GRAPHICS]The first spirocyclic nucleoside featuring a beta -hydroxyl (anti) at C5' has yielded to synthesis. While the OMOM functionality proved to be sensitive to the conditions necessary to incorporate heterocyclic bases, PMB protection of the carbinol was readily accommodated. The remarkably similar minimum-energy conformations of, the title compounds relative to natural thymidine as deduced by: Amber calculations in the gas phase are noted.

  DOI：

  10.1021/ol010212g
• 作为产物：
  描述：

  Acetic acid (2R,3R,4S,5R,6R)-3-acetoxy-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-6-(4-methoxy-benzyloxy)-1-oxa-spiro[4.4]non-4-yl ester 在 水 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 以91%的产率得到Acetic acid (2R,3R,4S,5R,6R)-3-acetoxy-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-6-hydroxy-1-oxa-spiro[4.4]non-4-yl ester
  参考文献：
  名称：

  Spirocyclic Restriction of Nucleosides. An Analysis of Protecting Group Feasibility while Accessing Prototype anti-1-Oxaspiro[4.4]nonanyl Mimics

  摘要：

  [GRAPHICS]The first spirocyclic nucleoside featuring a beta -hydroxyl (anti) at C5' has yielded to synthesis. While the OMOM functionality proved to be sensitive to the conditions necessary to incorporate heterocyclic bases, PMB protection of the carbinol was readily accommodated. The remarkably similar minimum-energy conformations of, the title compounds relative to natural thymidine as deduced by: Amber calculations in the gas phase are noted.

  DOI：

  10.1021/ol010212g