(3aS,4S,6aR)-4-(2-methoxy-2-oxoethyl)-2,2-dimethyl-6-[(trityloxy)methyl]-4,6a-dihydro-3aH-[1,3]dioxolo[4,5-c]pyrrol-5-ium-5-olate

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (3aS,4S,6aR)-4-(2-methoxy-2-oxoethyl)-2,2-dimethyl-6-[(trityloxy)methyl]-4,6a-dihydro-3aH-[1,3]dioxolo[4,5-c]pyrrol-5-ium-5-olate
• 英文别名: methyl 2-[(3aR,6S,6aS)-2,2-dimethyl-5-oxido-4-(trityloxymethyl)-6,6a-dihydro-3aH-[1,3]dioxolo[4,5-c]pyrrol-5-ium-6-yl]acetate
• 化学式: C₃₀H₃₁NO₆
• 分子量: 501.579
• InChiKey: BLBKDONWGQLJLJ-SAAIGDAKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  37
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  82.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  5-O-三苯甲基-2,3-O-异亚丙基-D-呋喃核糖 在 重铬酸吡啶 、 3 A molecular sieve 、 盐酸羟胺 、 碳酸氢钠 、 溶剂黄146 、 苯甲酸 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 20.5h， 生成 (3aS,4S,6aR)-4-(2-methoxy-2-oxoethyl)-2,2-dimethyl-6-[(trityloxy)methyl]-4,6a-dihydro-3aH-[1,3]dioxolo[4,5-c]pyrrol-5-ium-5-olate
  参考文献：
  名称：

  Synthesis of enantiomerically pure hydroxylated pyrroline N-oxides from d-ribose

  摘要：

  A convenient way to obtain enantiomerically pure hydroxylated pyrroline N-oxides is reported. The key step is the formation of omega-oxo criciates from (D)-ribose and a subsequent 1,3-azaprotio cyclotransfer reaction of the resulting oximino alkenoate derivatives. The stereochemistry of the nitrones obtained is discussed in relation to that of the starting compounds. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.02.006

文献信息

• Synthesis of enantiomerically pure hydroxylated pyrroline N-oxides from d-ribose
  作者：Nikolaos G. Argyropoulos、Theodoros D. Panagiotidis、John K. Gallos

  DOI：10.1016/j.tetasy.2006.02.006

  日期：2006.3

  A convenient way to obtain enantiomerically pure hydroxylated pyrroline N-oxides is reported. The key step is the formation of omega-oxo criciates from (D)-ribose and a subsequent 1,3-azaprotio cyclotransfer reaction of the resulting oximino alkenoate derivatives. The stereochemistry of the nitrones obtained is discussed in relation to that of the starting compounds. (c) 2006 Elsevier Ltd. All rights reserved.