(1S,2S,3S,7aS)-hexahydro-3-((S)-1,2-dihydroxyethyl)-1H-pyrrolizine-1,2-diol | 948897-83-4

• 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: (1S,2S,3S,7aS)-hexahydro-3-((S)-1,2-dihydroxyethyl)-1H-pyrrolizine-1,2-diol
• 英文别名: (1S,2S,3S,8S)-3-[(1S)-1,2-dihydroxyethyl]-2,3,5,6,7,8-hexahydro-1H-pyrrolizine-1,2-diol
• CAS: 948897-83-4
• 化学式: C₉H₁₇NO₄
• 分子量: 203.238
• InChiKey: OXLUKGWOSYORHL-BGKGJTHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  84.2
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-((2S,3S,4S,5S)-5-((S)-1,2-bis(benzyloxy)ethyl)-3,4-bis(benzyloxy)pyrrolidin-2-yl)propionic acid ethyl ester 在 三氯化硼 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 15.0h， 以75%的产率得到(1S,2S,3S,7aS)-hexahydro-3-((S)-1,2-dihydroxyethyl)-1H-pyrrolizine-1,2-diol
  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.