3,5-diazido-3,5-dideoxy-1,2-O-isopropylidene-α-D-xylofuranose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,5-diazido-3,5-dideoxy-1,2-O-isopropylidene-α-D-xylofuranose
• 英文别名: 1,2-O-isopropylidene-3,5-di-azido-3,5-dideoxy-α-d-xylofuranoside；3,5-diazido-3,5-dideoxy-1,2-O-isopropylidene-α-D-pentafuranose；(3aR,5R,6S,6aR)-6-azido-5-(azidomethyl)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole
• 化学式: C₈H₁₂N₆O₃
• 分子量: 240.222
• InChiKey: WTFICEWCYTYABE-XZBKPIIZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  56.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3,5-diazido-3,5-dideoxy-1,2-O-isopropylidene-α-D-xylofuranose 在 三氟乙酸 作用下， 以 水 为溶剂， 反应 3.25h， 生成
  参考文献：
  名称：

  二羟基化的4-氨基和5-氨基亚氨基糖的合成，构象研究，糖苷酶抑制活性和分子对接研究。

  摘要：

  报道了一种从D-葡萄糖开始合成新的氨基亚氨基糖6a，7a和8的有效方法。使用（1）H NMR数据进行的构象研究表明，氨基亚氨基糖6a存在于（2）C5中；7a和8以（5）C2构象存在。不同糖苷酶的抑制活性表明6a和7a是不良的糖苷酶抑制剂。然而，氨基亚氨基糖8显示出对β-半乳糖苷酶的选择性抑制（IC50 = 43μM，Ki = 153μM）。这些结果通过分子对接研究得到证实。

  DOI：

  10.1016/j.carres.2015.03.004
• 作为产物：
  描述：

  1,2:3,5-双-O-异亚丙基-alpha-D-呋喃木糖 在 15-冠醚-5 、 18-冠醚-6 吡啶 、 盐酸 、 sodium tetrahydroborate 、 重铬酸吡啶 、 sodium azide 、 乙醇 、 tetrabutylammonium tetrafluoroborate 、 水 、 sodium methylate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 、 1,2-二氯乙烷 为溶剂， 反应 16.0h， 生成 3,5-diazido-3,5-dideoxy-1,2-O-isopropylidene-α-D-xylofuranose
  参考文献：
  名称：

  Synthesis of Different 3,5‐Diazidofuranoses: A New and General Synthesis Pathway

  摘要：

  Diamino- and diazidofuranoses represent useful precursors, for example, for the synthesis of substituted nucleosides and metal complexes, respectively. Known procedures for their synthesis lack the availability of cheap starting materials, adequate yields, and the access to all possible diastereomeres. Therefore, 3,5-diazido-3,5-dideoxy- and - 2,3,5- trideoxyfuranoses both with ribo- and xylo- configuration were prepared using different approaches.

  DOI：

  10.1080/07328300701540175

文献信息

• Ruthenium and osmium complexes of novel carbohydrate derived salen ligands: Synthesis, characterization and in situ ligand reduction
  作者：Soumik Mandal、Santanu Mandal、Dipravath K. Seth、Balaram Mukhopadhyay、Parna Gupta

  DOI：10.1016/j.ica.2012.12.016

  日期：2013.3

  bis-imino derivative H 2 L2 . The ligand H 2 L2 has been transformed to H 2 L3 upon reduction of one of the imine bonds in consequence to the oxidation of the leaving PPh 3 group to POPh 3 . Systematic spectroscopic characterization, 1 H and 13 C NMR, mass spectrometry, electronic spectra reveals the composition of the complexes. X-ray crystal structures of both the complexes are reported. Detailed

  摘要报道了具有碳水化合物衍生的salen配体和原位配体还原的两种钌（II）和（II）配合物（1和2）的合成和表征。在水杨醛存在下，使用连续流动氢反应器通过催化氢化反应还原1,2-O-异亚丙基-3,5-二叠氮基-3,5-二脱氧-α-d-吡喃吡喃糖苷（L1）导数H 2 L2。当亚胺键之一还原时，由于离开的PPh 3基团氧化成POPh 3，配体H 2 L2已转化为H 2 L3。系统的光谱表征，1 H和13 C NMR，质谱，电子光谱揭示了配合物的组成。报道了两种配合物的X射线晶体结构。
• Sugars to Control Ligand Shape in Metal Complexes: Conformationally Constrained Glycoligands with a Predetermination of Stereochemistry and a Structural Control
  作者：Ludivine Garcia、Stéphane Maisonneuve、Juan Xie、Régis Guillot、Pierre Dorlet、Eric Rivière、Michel Desmadril、François Lambert、Clotilde Policar

  DOI：10.1021/ic1002379

  日期：2010.8.16

  In coordination chemistry, ligand shape can be used to tune properties, such as metal selectivity, coordination number, electronic structure, redox potential, and metal center stereochemistry including coordination helicates formation, and also to generate cavities for encapsulation. The results presented in this article indicate that two epimeric glycoligands (3 and 4) based on the conformationally

  在配位化学中，配体形状可用于调节特性，例如金属选择性，配位数，电子结构，氧化还原电势和金属中心立体化学（包括配位螺旋），还可以生成用于封装的腔体。本文中呈现的结果表明两个差向异构glycoligands（3和4基于所述构象约束）低聚木糖-和核糖-1,2- ö -isopropylidenefurano支架是在水通过π-π堆积预组织由于疏水相互作用，证明从准分子观察。固态获得的一种Cu（II）配合物的结构（5）是手性的，由于两个配体绕Cu-Cu轴盘绕而产生原始的螺旋手性。它显示了一种不寻常的双层结构，如电子顺磁共振所表明的那样，在两个三唑基-吡啶基环之间存在π-π相互作用，并且在两个Cu（II）离子之间具有一个小的空穴，能够容纳桥连的水分子。来自差向异构体配体（6）的Cu（II）配合物在Cu（II）的d-d区域具有类似的CD镜像性质。由C3构型6和5引起的糖配体在金属中心有一个手性的预先确定
• Intrinsically Fluorescent Glycoligands To Study Metal Selectivity
  作者：Ludivine Garcia、Stéphane Maisonneuve、Jennifer Oudinet-Sin Marcu、Régis Guillot、François Lambert、Juan Xie、Clotilde Policar

  DOI：10.1021/ic200897v

  日期：2011.11.21

  Glycoligands are a versatile family of ligands centered on a sugar platform and functionalized by Lewis bases. In this article, pentofuranoses were appended with the fluoroionophores 4-(pyridin-2'-yl)-1,2,3-triazol-1-yl and 4-(2',1',3'-benzothiadiazol-4'-yl)-1,2,3-triazol-1-yl using the "click-like" cycloaddition [2 + 3] of Huisgen catalyzed by copper(I). Their fluorescence properties were used to study metal cation complexation. A possible selective functionalization of furanoscaffolds allows the synthesis of "mixed" glycoligands with the successive insertion of these different fluoroionophores. The metal selectivity and the chelating behavior of these six resulting intrinsically fluorescent glycoligands were investigated. The change in the configuration at the carbon C3 of furanose did not influence either the metal selectivity or the binding constants. However, different selectivities and binding constants were found to depend on the nature of the fluoroionophore moieties. Overall, the triazolylbenzothiadiazolyl chelating group was shown to be less efficient than the triazolylpyridyl claw for complexation. Interestingly enough, the triazolylbenzothiadiazolyl claw, which fluoresces in the visible range, did not interfere in the binding and selectivity of the more efficient triazolylpyridyl claw. This study suggests that the triazolylbenzothiadiazolyl moiety could be used as an adequate fluorescent reporter to qualitatively monitor complexation of other moieties.
• Synthesis of Different 3,5‐Diazidofuranoses: A New and General Synthesis Pathway
  作者：Daniel Koth、Andrea Fiedler、Sandy Scholz、Michael Gottschaldt

  DOI：10.1080/07328300701540175

  日期：2007.9

  Diamino- and diazidofuranoses represent useful precursors, for example, for the synthesis of substituted nucleosides and metal complexes, respectively. Known procedures for their synthesis lack the availability of cheap starting materials, adequate yields, and the access to all possible diastereomeres. Therefore, 3,5-diazido-3,5-dideoxy- and - 2,3,5- trideoxyfuranoses both with ribo- and xylo- configuration were prepared using different approaches.
• Synthesis, conformational study, glycosidase inhibitory activity and molecular docking studies of dihydroxylated 4- and 5-amino-iminosugars
  作者：Vijay M. Kasture、Navnath B. Kalamkar、Roopa J. Nair、Rakesh S. Joshi、Sushma G. Sabharwal、Dilip D. Dhavale

  DOI：10.1016/j.carres.2015.03.004

  日期：2015.5

  An efficient methodology for the synthesis of new amino iminosugars 6a, 7a and 8, starting from D-glucose, is reported. The conformational study using (1)H NMR data showed that the amino iminosugar 6a exists in the (2)C5 while; the 7a and 8 exist in the (5)C2 conformation. The inhibition activities with different glycosidases showed that 6a and 7a are poor glycosidase inhibitors. However, amino iminosugar

  报道了一种从D-葡萄糖开始合成新的氨基亚氨基糖6a，7a和8的有效方法。使用（1）H NMR数据进行的构象研究表明，氨基亚氨基糖6a存在于（2）C5中；7a和8以（5）C2构象存在。不同糖苷酶的抑制活性表明6a和7a是不良的糖苷酶抑制剂。然而，氨基亚氨基糖8显示出对β-半乳糖苷酶的选择性抑制（IC50 = 43μM，Ki = 153μM）。这些结果通过分子对接研究得到证实。