[(2R,4aR,6R,7R,7aS)-2-(benzenesulfonylmethyl)-6-(2,4-dioxopyrimidin-1-yl)-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3]dioxin-7-yl] acetate | 943856-03-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2R,4aR,6R,7R,7aS)-2-(benzenesulfonylmethyl)-6-(2,4-dioxopyrimidin-1-yl)-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3]dioxin-7-yl] acetate
• CAS: 943856-03-9
• 化学式: C₁₉H₂₀N₂O₉S
• 分子量: 452.442
• InChiKey: SRFFZXIHJITDLW-SOVHRIKKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  146
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  [(2R,4aR,6R,7R,7aS)-2-(benzenesulfonylmethyl)-6-(2,4-dioxopyrimidin-1-yl)-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3]dioxin-7-yl] acetate 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以87%的产率得到1-[(2R,4aR,6R,7R,7aR)-2-(benzenesulfonylmethyl)-7-hydroxy-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3]dioxin-6-yl]pyrimidine-2,4-dione
  参考文献：
  名称：

  Probing of PSE acetal protection for nucleoside chemistry

  摘要：

  The use of phenylsulfonylethylidene (PSE) acetal as a new 3 ',5 '-bridged protecting group in nucleoside chemistry is reported. The PSE acetal demonstrates to be compatible with Lewis acids used in standard glycosylation reactions. In addition, a selective 2 '-O-deacylation from a 3 ',5'-O-(phenylsulfonyl)-2 '-O-acetyl nucleoside can be achieved, giving access to subsequent chemical modifications in 2 ' position. However, the PSE acetal cleavage surprisingly appeared to be purine/pyrimidine base dependent. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.03.153
• 作为产物：
  描述：

  1,2-O-异亚丙基-alpha-D-呋喃木糖 在 苯磺酰胺 、 四丁基溴化铵 、 sodium hydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 45.0h， 生成 [(2R,4aR,6R,7R,7aS)-2-(benzenesulfonylmethyl)-6-(2,4-dioxopyrimidin-1-yl)-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3]dioxin-7-yl] acetate
  参考文献：
  名称：

  Probing of PSE acetal protection for nucleoside chemistry

  摘要：

  The use of phenylsulfonylethylidene (PSE) acetal as a new 3 ',5 '-bridged protecting group in nucleoside chemistry is reported. The PSE acetal demonstrates to be compatible with Lewis acids used in standard glycosylation reactions. In addition, a selective 2 '-O-deacylation from a 3 ',5'-O-(phenylsulfonyl)-2 '-O-acetyl nucleoside can be achieved, giving access to subsequent chemical modifications in 2 ' position. However, the PSE acetal cleavage surprisingly appeared to be purine/pyrimidine base dependent. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.03.153