(5S,6S,7S,7aS)-hexahydro-6,7-dihydroxy-5-((S)-1,2-dihydroxyethyl)pyrrolizin-3-one | 948897-80-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯里西啶类
• 英文名称: (5S,6S,7S,7aS)-hexahydro-6,7-dihydroxy-5-((S)-1,2-dihydroxyethyl)pyrrolizin-3-one
• 英文别名: (5S,6S,7S,8S)-5-[(1S)-1,2-dihydroxyethyl]-6,7-dihydroxy-1,2,5,6,7,8-hexahydropyrrolizin-3-one
• CAS: 948897-80-1
• 化学式: C₉H₁₅NO₅
• 分子量: 217.222
• InChiKey: PJRXQIXRWWYCLB-OFKRZXBASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  101
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (5S,6S,7S,7aS)-5-((S)-1,2-bis(benzyloxy)ethyl)-6,7-bis(benzyloxy)-hexahydropyrrolizin-3-one 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 96.0h， 以57%的产率得到(5S,6S,7S,7aS)-hexahydro-6,7-dihydroxy-5-((S)-1,2-dihydroxyethyl)pyrrolizin-3-one
  参考文献：
  名称：

  Stereoselective synthesis of β-1-C-substituted 1,4-dideoxy-1,4-imino-d-galactitols and evaluation as UDP-galactopyranose mutase inhibitors

  摘要：

  The synthesis of 1-C-substituted 1,4-dideoxy-1,4-imino-D-galactitols involving nitrone umpolung is described. The SmI2-induced key coupling proved highly stereoselective in favor of the beta-C-substituted products bearing a three-carbon chain at the pseudoanomeric position. Pyrrolidines 9 and 10, as well as the bicyclic compounds 8 and 11, exhibit weak inhibition of the activity of the UDP-galactopyranose mutase from Escherichia coli. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.06.059

文献信息

• Stereoselective synthesis of β-1-C-substituted 1,4-dideoxy-1,4-imino-d-galactitols and evaluation as UDP-galactopyranose mutase inhibitors
  作者：Stéphanie Desvergnes、Valérie Desvergnes、Olivier R. Martin、Kenji Itoh、Hung-wen Liu、Sandrine Py

  DOI：10.1016/j.bmc.2007.06.059

  日期：2007.10

  The synthesis of 1-C-substituted 1,4-dideoxy-1,4-imino-D-galactitols involving nitrone umpolung is described. The SmI2-induced key coupling proved highly stereoselective in favor of the beta-C-substituted products bearing a three-carbon chain at the pseudoanomeric position. Pyrrolidines 9 and 10, as well as the bicyclic compounds 8 and 11, exhibit weak inhibition of the activity of the UDP-galactopyranose mutase from Escherichia coli. (C) 2007 Elsevier Ltd. All rights reserved.