(2R,3R,4S)-4-azido-2-(dimethoxymethyl)tetrahydrofuran-3-ol | 136024-94-7

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (2R,3R,4S)-4-azido-2-(dimethoxymethyl)tetrahydrofuran-3-ol
• 英文别名: (2R,3R,4S)-4-azido-2-(dimethoxymethyl)oxolan-3-ol
• CAS: 136024-94-7
• 化学式: C₇H₁₃N₃O₄
• 分子量: 203.198
• InChiKey: MGCUPLPFEYKGAU-KVQBGUIXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  62.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S)-4-azido-2-(dimethoxymethyl)tetrahydrofuran-3-ol 在 N-溴代丁二酰亚胺(NBS) 、 水 、 sodium hydride 、 potassium carbonate 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙腈 、 mineral oil 为溶剂， 反应 29.5h， 生成 (2R,3R,4S)-methyl 4-azido-3-(benzyloxy)tetrahydrofuran-2-carboxylate
  参考文献：
  名称：

  用于折叠聚体和肽纳米管的环状γ-氨基酸的合成

  摘要：

  环状γ-氨基酸是肽和折叠体化学中非常受关注的分子构建块，因为它们允许制备自然界中未发现的新结构。在本文中，我们描述了在氨基和羧酸基团之间具有顺式关系的环状 γ-氨基酸的合成。在大多数情况下，这种排列会导致生成的肽采用扁平构象，这使得它们适用于采用 β-折叠型结构的折叠体的设计。

  DOI：

  10.1002/ejoc.201201565
• 作为产物：
  描述：

  在 sodium azide 、 ammonium chloride 、 potassium carbonate 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 24.0h， 生成 (2R,3R,4S)-4-azido-2-(dimethoxymethyl)tetrahydrofuran-3-ol
  参考文献：
  名称：

  Synthesis of some pyrrolo[2,3-d]pyrimidine and 1,2,3-triazole isonucleosides

  摘要：

  Nucleoside analogues 8, 9, 10 and 11, in which a pyrrolo[23-d]pyrimidine ring is linked to a 2-hydroxymethyl-3-hydroxytetrahydrofuran, have been prepared. The azide 16 used as an intermediate in the routes to these compounds also gave access to the 1, 2, 3-triazole isonucleosides 12 and 13. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00102-6

文献信息

• Design, synthesis, and preliminary evaluation of the biological activity of dithiocarbamate-3-epi-jaspine B hybrids
  作者：En Zhang、Wei-Wei Jiao、Shang Wang、Jin-Mei Xu、Xiao-Jing Shi、Yan-Chao Wang、Ya-Na Wang、Hong-Min Liu

  DOI：10.1007/s00044-016-1721-9

  日期：2016.12

  dithiocarbamate-3-epi-jaspine B hybrids have been designed and synthesized from D-xylose based on the introduction of long lipophilic alkyl dithiocarbamate moieties at the C4 position of 3-epi-jaspine B. The anticancer activities of these compounds have been evaluated against two selected tumor cell lines (MGC-803 and B16-F10 cells), with most of the synthesized compounds exhibiting moderate activity. Among them, compounds

  在D-木糖的基础上，基于在3- epi- jaspine B的C4位置引入了长亲脂性烷基dithiocarbamate烷基部分，设计并合成了一系列dithiocarbamate -3- epi - jaspine B杂种。这些化合物的抗癌活性具有已针对两种选定的肿瘤细胞系（MGC-803和B16-F10细胞）进行了评估，大多数合成化合物均表现出中等活性。其中，化合物20d和2 0f在所有测试的化合物中对IC 50为MGC-803和B16-F10细胞的抑制活性最高值分别为16.39和14.83 µM。因此，这项工作代表了第一个报道的二硫代氨基甲酸酯-3-表位-茉莉B杂种的合成和体外细胞毒性评估。
• <i>cis</i>-Platinum Complex Encapsulated in Self-Assembling Cyclic Peptide Dimers
  作者：Nuria Rodríguez-Vázquez、Rebeca García-Fandiño、María J. Aldegunde、José Brea、María Isabel Loza、Manuel Amorín、Juan R. Granja

  DOI：10.1021/acs.orglett.7b00871

  日期：2017.5.19

  A new cyclic peptide dimer that encapsulates cisplatin complexes in its internal cavity is described. The resulting complex showed cytotoxic activity at A2780 ovarian cancer cell lines independent of acquired platinum resistance.

  描述了一种新的环状肽二聚体，其在其内部空腔中包裹了顺铂复合物。所得复合物在A2780卵巢癌细胞系中显示出细胞毒性活性，而与获得的铂抗性无关。
• α,γ-Cyclic peptide ensembles with a hydroxylated cavity
  作者：César Reiriz、Manuel Amorín、Rebeca García-Fandiño、Luis Castedo、Juan R. Granja

  DOI：10.1039/b911247m

  日期：——

  Here we describe a self-assembling α,γ-cyclic tetrapeptide that contains the 4-amino-3-hydroxytetrahydrofuran-2-carboxylic acid, in which the hydroxy group is pointing towards the inner cavity of the resulting dimers.

  在这里，我们描述了一种含有 4-氨基-3-羟基四氢呋喃-2-羧酸的自组装δ,δ-环四肽，其中的羟基指向所得二聚体的内腔。
• Synthesis and preliminary biological evaluation of 1,2,3-triazole-Jaspine B hybrids as potential cytotoxic agents
  作者：Jin-Mei Xu、En Zhang、Xiao-Jing Shi、Yan-Chao Wang、Bin Yu、Wei-Wei Jiao、Ya-Zhuo Guo、Hong-Min Liu

  DOI：10.1016/j.ejmech.2014.03.022

  日期：2014.6

  Two series of more available novel 1,2,3-triazole-Jaspine B hybrids were efficiently synthesized employing click chemistry approach and evaluated for their cytotoxic activities against three human cancer cell lines (EC-9706, MGC-803 and MCF-7). Among them, compound 14h showed excellent inhibition against MCF-7 (IC50 = 1.93 μM) and was more potent than 5-Fu and Jaspine B against all three cancer cell lines. Further investigation of apoptosis assay and cell cycle analysis demonstrated that compound 14h caused cellular early and late apoptosis and arrested the cell cycle at G2/M phase in a concentration- and time-independent manner. This was the first report about the synthesis and in vitro cytotoxic evaluation of 1,2,3-triazole-Jaspine B hybrids.
• An efficient and convenient formal synthesis of Jaspine B from d-xylose
  作者：Ming-Li Zhao、En Zhang、Jie Gao、Zhao Zhang、Yu-Tao Zhao、Wen Qu、Hong-Min Liu

  DOI：10.1016/j.carres.2012.01.013

  日期：2012.4

  A formal synthesis of Jaspine B was completed in 42.4% overall yield with only three purification steps (one by crystallization and two by column chromatography). The key step in the synthesis involves a regio- and stereoselective epoxide ring-opening reaction and the configuration inversion of the C3-hydroxyl group through oxidation and reduction. All of the reagents and materials used were quite common and inexpensive. (C) 2012 Elsevier Ltd. All rights reserved.