(1R,2S,3S,6S,7S,7aR)-1,2,6,7-tetrahydroxy-3-hydroxymethylpyrrolizidine | 1609382-22-0

• 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: (1R,2S,3S,6S,7S,7aR)-1,2,6,7-tetrahydroxy-3-hydroxymethylpyrrolizidine
• 英文别名: (1R,2S,3S,6S,7S,7aR)-3-(hydroxymethyl)hexahydro-1H-pyrrolizine-1,2,6,7-tetraol；2,3-epi-casuarine；(1R,2S,3S,6S,7S,8R)-3-(hydroxymethyl)-2,3,5,6,7,8-hexahydro-1H-pyrrolizine-1,2,6,7-tetrol
• CAS: 1609382-22-0
• 化学式: C₈H₁₅NO₅
• 分子量: 205.211
• InChiKey: AXTGOJVKRHFYBT-ANBNMOMCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.7
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  104
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1R,2S,3S,6S,7S,7aR)-1,2,6,7-tetrahydroxy-3-hydroxymethylpyrrolizidine 、 乙酸酐 在 吡啶 作用下， 以0.08 g的产率得到(1R,2S,3S,6S,7S,7aR)-3-(acetoxymethyl)hexahydro-1H-pyrrolizine-1,2,6,7-tetrayl tetraacetate
  参考文献：
  名称：

  Synthesis of analogues of hyacinthacines, casuarine and uniflorine A from C-2 formyl galactal

  摘要：

  The synthesis of analogues of hyacinthacine, casuarine and uniflorine A is described. The key steps involved in achieving these targets are the zinc mediated Barbier reaction, vinyl Grignard reaction, dihydroxylation and cyclization. All of the synthesized compounds were tested against several glycosidases. Compound 11 showed selective inhibition against alpha-mannosidase (Jack beans) with an IC50 value of 81.2 mu M. On the other hand, compound 33 showed selective inhibition of alpha-glucosidases from Baker's yeast and rice with IC50 values of 68.0 and 96.0 mu M respectively. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2016.08.017
• 作为产物：
  描述：

  在 palladium hydroxide, 20 wt% on carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 48.0h， 生成 (1R,2S,3S,6S,7S,7aR)-1,2,6,7-tetrahydroxy-3-hydroxymethylpyrrolizidine
  参考文献：
  名称：

  Synthesis of analogues of hyacinthacines, casuarine and uniflorine A from C-2 formyl galactal

  摘要：

  The synthesis of analogues of hyacinthacine, casuarine and uniflorine A is described. The key steps involved in achieving these targets are the zinc mediated Barbier reaction, vinyl Grignard reaction, dihydroxylation and cyclization. All of the synthesized compounds were tested against several glycosidases. Compound 11 showed selective inhibition against alpha-mannosidase (Jack beans) with an IC50 value of 81.2 mu M. On the other hand, compound 33 showed selective inhibition of alpha-glucosidases from Baker's yeast and rice with IC50 values of 68.0 and 96.0 mu M respectively. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2016.08.017

文献信息

• Casuarine Stereoisomers from Achiral Substrates: Chemoenzymatic Synthesis and Inhibitory Properties
  作者：Alda Lisa Concia、Livia Gómez、Teodor Parella、Jesús Joglar、Pere Clapés

  DOI：10.1021/jo500991p

  日期：2014.6.6

  A straightforward chemoenzymatic synthesis of four uncovered casuarine stereoisomers is described. The strategy consists of L-fuculose-l-phosphate aldolase F131A-variant-catalyzed aldol addition of dihydroxyacetone phosphate to aldehyde derivatives of 1,4-dideoxy-1,4-imino-o-arabinitol (DAB) and its enantiomer (LAB) and subsequent one-pot catalytic deprotection reductive amination. DAB and LAB were obtained from dihydroxyacetone and aminoethanol using D-fructose-6-phosphate aldolase and L-rhamnulose-l-phosphate aldolase catalysts, respectively. The new ent-3-epi-casuarine is a strong inhibitor of alpha-D-glucosidase from rice and of rat intestinal sucrase.