methyl (R)-5-hydroxycarbonyl-5-methyl-2,2-dioxo-2λ⁶-[1,2,3]oxathiazolidine-3-carboxylate | 1022223-87-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机硫酸及其衍生物
• 英文名称: methyl (R)-5-hydroxycarbonyl-5-methyl-2,2-dioxo-2λ⁶-[1,2,3]oxathiazolidine-3-carboxylate
• 英文别名: (5R)-3-methoxycarbonyl-5-methyl-2,2-dioxooxathiazolidine-5-carboxylic acid
• CAS: 1022223-87-5
• 化学式: C₆H₉NO₇S
• 分子量: 239.206
• InChiKey: JJTOPQRGWMDMOK-ZCFIWIBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  119
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  methyl (R)-5-(methoxymethylcarbamoyl)-5-methyl-2,2-dioxo-2λ⁶-[1,2,3]oxathiazolidine-3-carboxylate 在 硫酸 作用下， 以 水 为溶剂， 反应 48.0h， 以94%的产率得到methyl (R)-5-hydroxycarbonyl-5-methyl-2,2-dioxo-2λ⁶-[1,2,3]oxathiazolidine-3-carboxylate
  参考文献：
  名称：

  Highly chemoselective reactions on hindered sulfamidates with oxygenated nucleophiles

  摘要：

  Although the chemoselectivity problems in substitution reactions, which arise from the use of oxygenated nucleophiles in a basic medium by generating anionic species are well-known, we report herein a highly chemoselective ring-opening reaction of hindered cyclic sulfamidates with O-nucleophiles. The reaction occurs with the inversion of configuration at the quaternary centre, allowing the stereoselective synthesis of an important class of beta(2,2)-amino acids, namely O-substituted alpha-methylisoserines. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.01.030

文献信息

• Highly chemoselective reactions on hindered sulfamidates with oxygenated nucleophiles
  作者：Gonzalo Jiménez-Osés、Alberto Avenoza、Jesús H. Busto、Jesús M. Peregrina

  DOI：10.1016/j.tetasy.2008.01.030

  日期：2008.3

  Although the chemoselectivity problems in substitution reactions, which arise from the use of oxygenated nucleophiles in a basic medium by generating anionic species are well-known, we report herein a highly chemoselective ring-opening reaction of hindered cyclic sulfamidates with O-nucleophiles. The reaction occurs with the inversion of configuration at the quaternary centre, allowing the stereoselective synthesis of an important class of beta(2,2)-amino acids, namely O-substituted alpha-methylisoserines. (C) 2008 Elsevier Ltd. All rights reserved.