benzyl (2S,3R,4R)-3,4-dihydroxy-2-[(1S,2R)-1,2,4-trihydroxy-3-oxobutyl]pyrrolidine-1-carboxylate | 1609382-18-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl (2S,3R,4R)-3,4-dihydroxy-2-[(1S,2R)-1,2,4-trihydroxy-3-oxobutyl]pyrrolidine-1-carboxylate
• CAS: 1609382-18-4
• 化学式: C₁₆H₂₁NO₈
• 分子量: 355.345
• InChiKey: UHEZSADQUAUKCO-BFYSQQLMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  148
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  benzyl (2S,3R,4R)-3,4-dihydroxy-2-[(1S,2R)-1,2,4-trihydroxy-3-oxobutyl]pyrrolidine-1-carboxylate 在 palladium on activated charcoal 、 氢气 作用下， 以 甲醇 、 水 为溶剂， 20.0 ℃ 、344.75 kPa 条件下， 以8%的产率得到(1R,2S,3R,6R,7R,7aS)-1,2,6,7-tetrahydroxy-3-hydroxymethylpyrrolizidine
  参考文献：
  名称：

  Casuarine Stereoisomers from Achiral Substrates: Chemoenzymatic Synthesis and Inhibitory Properties

  摘要：

  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.

  DOI：

  10.1021/jo500991p
• 作为产物：
  描述：

  benzyl 3,4-dihydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate 在 L-fuculose-1-phosphate aldolase F₁₃₁A variant 、 potassium chloride 、 2-碘酰基苯甲酸 作用下， 以 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 benzyl (2S,3R,4R)-3,4-dihydroxy-2-[(1S,2R)-1,2,4-trihydroxy-3-oxobutyl]pyrrolidine-1-carboxylate
  参考文献：
  名称：

  Casuarine Stereoisomers from Achiral Substrates: Chemoenzymatic Synthesis and Inhibitory Properties

  摘要：

  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.

  DOI：

  10.1021/jo500991p

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.