2,5-imino-2,4,5,6-tetradeoxy-D-gulo-heptitol | 1378939-50-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 2,5-imino-2,4,5,6-tetradeoxy-D-gulo-heptitol
• 英文别名: (2S,3R,5R)-5-(2-hydroxyethyl)-2-(hydroxymethyl)pyrrolidin-3-ol
• CAS: 1378939-50-4
• 化学式: C₇H₁₅NO₃
• 分子量: 161.201
• InChiKey: MYQUTXDAYVWUDH-DSYKOEDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  72.7
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (2R,3R,4R,5R)-2-[(1R)-1,9-dihydroxynonyl]-5-(hydroxymethyl)pyrrolidine-3,4-diol 生成 2,5-imino-2,4,5,6-tetradeoxy-D-gulo-heptitol
  参考文献：
  名称：

  Pyrrolidine-type iminosugars from leaves of Suregada glomerulata

  摘要：

  Phytochemical investigation of the H2O extract of leaves of Suregada glomerulata led to the isolation of ten pyrrolidine-type iminosugars. The chemical structures of the six new compounds (4-6, 8-10) were elucidated as 2,5-imino-2,4,5-trideoxy-D-manno-heptitol (4-deoxy-homoDMDP) (4), 2,5-imino-2,4, 5-trideoxy-D-gulo-heptitol (5), 2,5-imino-2,4,5,6-tetradeoxy-D-gulo-heptitol (6), 6-C-butyl-4-deoxy-DMDP (8), 6-C-(8-hydroxyoctyl)-DMDP (9), and 6-C-(8-hydroxyoctyl)-2,5-dideoxy-2,5-imino-D-galactitol (10), respectively, on the basis of spectroscopic data analysis (NMR and HRESIMS). Compounds 4-6 and 8 were characterized as rarely seen 4-deoxy pyrrolidine-type iminosugars. Pyrrolidine-type iminosugars with a long-side chain have been found in the restrictive plant families Moraceae, Campanulaceae, and Hyacinthaceae. The discovery of compounds 9 and 10 with a C-8 side chain from S. glomerulata (Euphorbiaceae) expands the range of distribution for the iminosugars in plants. The 8-hydroxyoctyl side-chain represents a new addition for the molecular diversity of iminosugars. The compounds 1-10 were evaluated for inhibitory activity against rat intestinal alpha-glucosidase. However, all the test compounds showed no significant inhibitory activities to the glucosidase. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.11.004