(2R,3S,4R)-N-tert-butoxycarbonyl-2-formyl-3,4-O-isopropylidenepyrrolidine-3,4-diol | 1189331-75-6

• 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: (2R,3S,4R)-N-tert-butoxycarbonyl-2-formyl-3,4-O-isopropylidenepyrrolidine-3,4-diol
• 英文别名: tert-butyl (3aS,4R,6aR)-2,2-dimethyl-4-formyldihydro-3aH-[1,3]dioxolane[4,5-c]pyrrol-5-(4H)-carboxylate；tert-butyl (3aS,4R,6aR)-4-formyl-2,2-dimethyl-3a,4,6,6a-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate
• CAS: 1189331-75-6
• 化学式: C₁₃H₂₁NO₅
• 分子量: 271.313
• InChiKey: WHPNXNRBVFQHLV-AEJSXWLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3S,4R)-N-tert-butoxycarbonyl-2-formyl-3,4-O-isopropylidenepyrrolidine-3,4-diol 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 0.83h， 以97%的产率得到(2S,3S,4R)-N-tert-butoxycarbonyl-2-hydroxymethyl-3,4-O-isopropylidenepyrrolidine-3,4-diol
  参考文献：
  名称：

  Tuning of β-glucosidase and α-galactosidase inhibition by generation and in situ screening of a library of pyrrolidine-triazole hybrid molecules

  摘要：

  The preliminary screening of two libraries of epimeric (pyrrolidin-2-yl)triazoles (14a-s and 22a-s), generated via click chemistry, allowed the rapid identification of four alpha-galactosidase (coffee beans) inhibitors (22b,k,p,r) and two beta-glucosidase (almond) inhibitors (14b,f) in the low mu M range. The additional biological analysis of 14b,f towards beta-glucocerebrosidase (human lysosomal beta-glucosidase), as target enzyme for Gaucher disease, showed a good correlation with the inhibition results obtained for the plant (almond) enzyme. Surprisingly, although these compounds showed inhibition towards beta-glucocerebrosidase as acid hydrolase, they did not inhibit bovine liver beta-glucosidase as neutral hydrolase. In contrast to what was observed for beta-glucosidase inhibition, the coffee bean alpha-galactosidase inhibitors of the epimeric library (22b,k,p,r) only showed weak inhibition towards human lysosomal alpha-galactosidase. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.06.055
• 作为产物：
  描述：

  tert-butyl (3aS,4S,6aR)-2,2-dimethyl-4-[(R)-1,2-dihydroxyethyl]dihydro-3aH-[1,3]dioxolane[4,5-c]pyrrol-5-(4H)-carboxylate 在 sodium periodate 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 以92%的产率得到(2R,3S,4R)-N-tert-butoxycarbonyl-2-formyl-3,4-O-isopropylidenepyrrolidine-3,4-diol
  参考文献：
  名称：

  一种含硫稠杂四环氮杂糖衍生物及其制备方 法

  摘要：

  本发明公开了一种含硫稠杂四环氮杂糖衍生物，它的化学通式如I所示，其制备方法包括以下步骤：（a）将五元氮杂糖醛和氨基酸酯盐酸盐混合后溶解于有机溶剂中，在40‑60℃下搅拌30‑60 min，加入巯基水杨酸或巯基烟酸，搅拌，在40‑100℃反应8‑15小时，调节反应液的pH值至中性，萃取，得到如化学通式IV所示的中间体化合物；（b）将中间体化合物IV，在酸性条件下脱除保护基，并碱性条件下酰胺化关环，得如化学通式I所示的含硫稠杂四环氮杂糖衍生物。本发明提供的含硫稠杂四环氮杂糖衍生物的制备方法简单、操作容易、易于规模化生产，制备的化合物I经过试验验证，其具有较强的HIV抑制活性，可在抗HIV病毒药物制剂中推广应用。

  公开号：

  CN104876950B

文献信息

• Structure and temperature controlled synthesis of novel thiazolidin-4-one derivatives bearing an azasugar
  作者：Hua Chen、Sinan Wei、Hongbo Zhang、Xiaoliu Li

  DOI：10.1016/j.tetasy.2013.03.006

  日期：2013.4

  Novel thiazolidin-4-one linked pseudo-aza-disaccharides and thiazolidin-4-ones containing C-pseudo-aza-nucleosides were synthesized via a one-pot three component reaction. The former was synthesized stereoselectively by the tandem Staudinger/aza-Wittig/cyclization reaction of azasugar aldehyde 1, an azidosugar, and mercaptoacetic acid. The reaction was structure and temperature controlled, and could be

  通过一锅三组分反应合成了新型的噻唑烷酮-4-酮连接的伪氮杂二糖和含有C-伪氮杂核苷的噻唑烷-4-酮。前者是通过串联的Staudinger / aza-Wittig /氮杂糖醛1，叠氮基糖和巯基乙酸的环化反应立体合成的。该反应是结构和温度受控的，并且可以在40℃下立体定向地进行。这是噻唑烷定-4-酮连接衍生物的立体有择合成的首次报道。然而，这些衍生物是通过使杜鹃糖醛1，苯胺和巯基乙酸发生缩合反应而以低的立体选择性合成的。
• Synthesis of tetracyclic iminosugars fused benzo[e][1,3]thiazin-4-one and their HIV-RT inhibitory activity
  作者：Zhuqing Yin、Mo Zhu、Sinan Wei、Jie Shao、Yuheng Hou、Hua Chen、Xiaoliu Li

  DOI：10.1016/j.bmcl.2016.02.049

  日期：2016.4

  groups, the target novel tetracyclic iminosugars fused benzo[e][1,3]thiazin-4-one 1(a–c) and 2(a–b) were first afforded by the intramolecular cyclo-amidation reaction. Their structures were determined by their 1H, 13C NMR, and HRMS (ESI) spectra and X-ray. The tetracyclic iminosugars 1(a–c) and 2(a–b) were examined for their HIV reverse transcriptase (RT) inhibitory activities. The result showed that

  几个氮杂Ç -pseudonucleosides轴承1,3-苯并噻嗪-4-酮（6和7）通过从所述亚氨基糖醛一锅三组分缩合制备3，氨基酸乙酯/甲基酯盐酸盐4（一- ç）和2-巯基苯甲酸5。除去Boc和异亚丙基后，目标新型四环亚氨基糖融合了苯并[ e ] [1,3]噻嗪-4-酮1（a – c）和2（a – b）首先通过分子内环酰胺化反应得到。它们的结构由1 H，13 C NMR和HRMS（ESI）光谱和X射线确定。检查了四环亚氨基糖1（a - c）和2（a - b）的HIV逆转录酶（RT）抑制活性。结果表明，所有化合物均可有效抑制RT活性。其中，化合物2a是最好的化合物，其RT抑制活性的IC 50值为0.82μM。结构-活性关系分析表明1'R 四环氮杂糖中的构型有利于其抗HIV RT活性。