1,2-di-O-acetyl-3,5-O-(2-phenylsulfonyl)ethylidene-D-xylofuranose | 943856-01-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: 1,2-di-O-acetyl-3,5-O-(2-phenylsulfonyl)ethylidene-D-xylofuranose
• 英文别名: [(2R,4aR,7R,7aS)-6-acetyloxy-2-(benzenesulfonylmethyl)-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3]dioxin-7-yl] acetate
• CAS: 943856-01-7
• 化学式: C₁₇H₂₀O₉S
• 分子量: 400.406
• InChiKey: BFOMGSGPAMDOTN-VDWCLKJHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  123
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1,2-di-O-acetyl-3,5-O-(2-phenylsulfonyl)ethylidene-D-xylofuranose 在 苯磺酰胺 、 potassium carbonate 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 23.0h， 生成 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：

  1,2:3,5-双-O-异亚丙基-alpha-D-呋喃木糖 在 盐酸 、 四丁基溴化铵 、 sodium hydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 33.0h， 生成 1,2-di-O-acetyl-3,5-O-(2-phenylsulfonyl)ethylidene-D-xylofuranose
  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