2-脱氧-1,5-脱水葡萄糖醇 | 3971-47-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 中文名称: 2-脱氧-1,5-脱水葡萄糖醇
• 英文名称: 1,5-anhydro-2-deoxy-D-lyxo-hexitol
• 英文别名: 1,5-anhydro-2-deoxy-D-galactitol；1,2-Deoxygalactose；(2R,3R,4R)-2-(hydroxymethyl)oxane-3,4-diol
• CAS: 3971-47-9
• 化学式: C₆H₁₂O₄
• 分子量: 148.159
• InChiKey: QFHKFGOUFKUPNX-HSUXUTPPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  69.9
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-脱氧-1,5-脱水葡萄糖醇 、 4-硝基苯基-D-吡喃葡糖苷 在 bovine testea β-galactosidase 、 McIlvain buffer 作用下， 以 水 为溶剂， 反应 50.0h， 以81%的产率得到
  参考文献：
  名称：

  Facile One‐Step Syntheses of ModifiedO‐Glycoprotein Galβ1‐3GalNAc Structures by Transglycosylation Employing Three β‐Galactosidases from Bovine Testes,Xanthomonas manihotis, andBacillus circulans

  摘要：

  Natural O-glycoproteins such as the Thomsen-Friedenreich antigen or gangliosides contain the motif Gal beta 1-3GalNAc as an important disaccharide with significant biologic activity. The arrangement of spatial functionalities in this structure are of particular interest with regard to the development of potential leads en route to pharmaceuticals. Therefore, it was desired to obtain access to a range of modified derivatives of the aforementioned motif paying particular attention to introducing specific deoxy functions instead of hydroxyl groups.

  DOI：

  10.1080/07328300500208131
• 作为产物：
  描述：

  (2R,3R,4R)-2-(羟基甲基)-3,4-二氢-2H-吡喃-3,4-二醇 在 palladium on activated charcoal 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 16.0h， 以1.1 g的产率得到2-脱氧-1,5-脱水葡萄糖醇
  参考文献：
  名称：

  Siglec-8 配体 6'-Sulfo-Sialyl Lewisx 的有效模拟物。

  摘要：

  Siglecs 是含有唾液酸结合 N 端结构域的免疫球蛋白基因家族的成员。其中，Siglec-8 在免疫系统的各种细胞类型上表达，如嗜酸性粒细胞、肥大细胞和弱碱性粒细胞。Siglec-8 与单克隆抗体的交联触发嗜酸性粒细胞凋亡并抑制肥大细胞脱颗粒，使 Siglec-8 成为治疗嗜酸性粒细胞和肥大细胞相关疾病（如哮喘）的有希望的靶点。四糖 6'-磺基唾液酸路易斯x已被鉴定为聚糖阵列筛选中的特定 Siglec-8 配体。在这里，我们描述了一项扩展研究，启发了 6'-磺基-唾液酸路易斯x的药效团并成功开发了一种高亲和力的模拟物。保留神经氨酸核心，在 9 位引入 Gal 部分的碳环模拟物和磺酰胺取代基使结合亲和力提高了 20 倍。最后，停留时间，通常是碳水化合物/凝集素相互作用的跟腱，可以得到改善。

  DOI：

  10.1002/cmdc.202000417

文献信息

• Controlling Sugar Deoxygenation Products from Biomass by Choice of Fluoroarylborane Catalyst
  作者：Youngran Seo、Jared M. Lowe、Michel R. Gagné

  DOI：10.1021/acscatal.9b01578

  日期：2019.8.2

  The feedstocks from biomass are defined and limited by nature, but through the choice of catalyst, one may change the deoxygenation outcome. We report divergent but selective deoxygenation of sugars with triethylsilane (TESH) and two fluoroarylborane catalysts, B(C6F5)3 and B(3,5-CF3)2C6H3)3 (BAr3,5-CF3). To illustrate, persilylated 2-deoxyglucose shows exocyclic C–O bond cleavage/reduction with the

  来自生物质的原料受到自然界的定义和限制，但是通过选择催化剂，可以改变脱氧的结果。我们报告了糖与三乙基硅烷（TESH）和两种氟芳基硼烷催化剂B（C 6 F 5）3和B（3,5-CF 3）2 C 6 H 3）3（BAr 3,5-CF3）的发散性但选择性脱氧）。为了说明这一点，全硅烷基化的2-脱氧葡萄糖显示出环外C–O键的裂解/还原与较少的空间拥挤的BAr 3,5-CF3，而环内的C–O键的裂解/还原则以路易斯酸B（C更多）为主6 F 5）3。取决于催化剂，可以选择性地合成手性呋喃和线性多元醇。机理研究表明，这些催化剂的静止状态是不同的。
• [EN] TARGETED NUCLEIC ACID CONJUGATE COMPOSITIONS<br/>[FR] COMPOSITIONS DE CONJUGUÉS D'ACIDES NUCLÉIQUES CIBLÉS
  申请人：PROTIVA BIOTHERAPEUTICS INC

  公开号：WO2017177326A1

  公开（公告）日：2017-10-19

  The invention provides conjugates that comprise a targeting moiety, a nucleic acid, and optional linking groups as well as synthetic intermediates and synthetic methods useful for preparing the conjugates. The conjugates are useful to target therapeutic nucleic acids to the liver and to treat liver diseases including hepatitis (e.g. hepatitis B and hepatitis D).

  这项发明提供了包括靶向基团、核酸和可选连接基团的共轭物，以及用于制备这些共轭物的合成中间体和合成方法。这些共轭物可用于将治疗性核酸靶向肝脏，并用于治疗包括肝炎（如乙型肝炎和丙型肝炎）在内的肝脏疾病。
• THE ACETOLYSIS OF SOME HYDROXYTETRAHYDRO-2-PYRANS
  作者：Thomas Francis、E. Von Rudloff

  DOI：10.1139/v59-131

  日期：1959.5.1

  The reaction between acetic anhydride and several hydroxytetrahydropyrans in the presence of boron trifluoride has been studied. 2-Methyl-3-hydroxytetrahydropyran, 2-hydroxymethyl-4,5-dihydroxytetrahydropyran, and 3,4-dihydroxytetrahydropyran all underwent normal acetolysis to the expected straight-chain polyol acetates. Optically active forms of cis-and trans-3,4-dihydroxytetrahydropyran gave the same, inactive pentanetetrol, showing that racemization of the active centers had accompanied ring cleavage. 2-Hydroxymethyl-tetrahydropyran gave 1,3,6-hexanetriol besides the expected 1,2,6-isomer. The reagent did not cleave 4-hydroxytetrahydropyran nor dihydro-D-galactal, but the latter underwent hydroxyl inversion to give dihydro-D-altral. 1,5-Anhydro-D-sorbitol (polygalitol) appeared to undergo both ring fission and inversion.

  已习得在三氟化硼存在下，醋酸酐与几种羟基四氢吡喃之间的反应。2-甲基-3-羟基四氢吡喃、2-羟甲基-4,5-二羟基四氢吡喃和3,4-二羟基四氢吡喃都经历了正常的醋酸解作用，生成了预期的直链多元醇醋酸酯。光学活性的顺式和反式3,4-二羟基四氢吡喃形成了相同的非活性戊糖醇，表明活性中心的消旋伴随着环裂解。2-羟甲基四氢吡喃除了生成预期的1,2,6-异构体外，还生成了1,3,6-己三醇。试剂不会裂解4-羟基四氢吡喃或二氢-D-半乳糖，但后者经历了羟基倒位，生成了二氢-D-阿尔半乳糖。1,5-去水-D-山梨醇（聚山梨醇）似乎经历了环裂解和倒位。
• Synthesis, characterization and dioxygen reactivity of copper(i) complexes with glycoligands
  作者：Ziad Damaj、Federico Cisnetti、Laurent Dupont、Eric Henon、Clotilde Policar、Emmanuel Guillon

  DOI：10.1039/b801109e

  日期：——

  A new family of copper(I) complexes with “glycoligands” containing a central saccharide scaffold, with 2-picolyl ether groups or 2-picolylamine or N-imidazolylamine groups, has been prepared and characterized. For this purpose, the following tetradentate ligands have been synthesized: methyl 2,3-di-O-(2-picolyl)-α-D-lyxofuranoside (L1), 1,5-anhydro-2-deoxy-3,4-di-O-(2-picolyl)-D-galactitol (L2), 5-(amino-N-(2-salicyl))-5-deoxy-1,2-O-isopropylidene-3-O-(2-picolyl)-α-D-xylofuranose (L3), and 5-(amino-N-(2-salicyl))-5-deoxy-1,2-O-isopropylidene-3-O-(methylimidazol-2-yl)-α-D-xylofuranose (L4). The ligands and the complexes were characterized by elemental analysis, IR, 1H and 13C NMR spectroscopies, ESI mass spectrometry, and cyclic voltammetry. Collaterally with the experimental work, HF-DFT(B3LYP/6–31G*) computations were performed to obtain additional structural information. The Cu(I) complexes are found to be pentacoordinated. The redox properties and the O2-reactivity of the CuILn complexes have been studied. Reactions of Cu(I) complexes with dioxygen in ethanol yield stable Cu(II) complexes as confirmed by UV-visible spectrophotometry and EPR spectroscopy.

  一个新的铜（I）络合物与“糖配体”包含一个中心糖支架，具有2-吡啶甲基醚基团或2-吡啶甲基胺或N-咪唑胺基团，已被制备和表征。为此，合成了以下四齿配体：甲基 2,3-二-O-(2-吡啶甲基)-α-D-lyxofuranoside (L1), 1,5-anHydro-2-deoxy-3,4-二-O-(2-吡啶甲基)-D-半乳糖醇 (L2), 5-(氨基-N-(2-水杨基))-5-脱氧-1,2-O-异亚丙基-3-O-(2-吡啶甲基）-α-D-呋喃木糖（L3）和 5-（氨基-N-（2-水杨基））-5-脱氧-1,2-O-异亚丙基-3-O-（甲基咪唑-2-基） -α-D-呋喃木糖 (L4)。通过元素分析、IR、1H 和 13C NMR 光谱、ESI 质谱和循环伏安法对配体和配合物进行了表征。在实验工作的同时，还进行了 HF-DFT(B3LYP/6–31G*) 计算以获得额外的结构信息。发现 Cu(I) 配合物是五配位的。研究了 CuILn 配合物的氧化还原性质和 O2 反应性。 Cu(I) 络合物与乙醇中的分子氧反应产生稳定的 Cu(II) 络合物，经紫外-可见分光光度法和 EPR 光谱法证实。
• Synthesis and X-ray crystal structures of two transition metal complexes based on functionalised 1,5-anhydro-2-deoxy-d-galactitol and methyl 2-deoxy-α-d-galactopyranoside
  作者：Federico Cisnetti、Régis Guillot、Nada Ibrahim、François Lambert、Michel Thérisod、Clotilde Policar

  DOI：10.1016/j.carres.2007.11.031

  日期：2008.2

  Two new ligands of transition metal cations based on galactose-derived scaffolds were synthesised: 1,5-anhydro-2-deoxy-3,4,6-tri-O-(2-picolyl)-D-galactitol and methyl 2-deoxy-3,4,6-tri-O-(2-picolyl)-alpha-D-galactopyranoside. These ligands permitted the isolation as single crystals of a Co(II) and a Ni(II) complex, respectively. The structures of both complexes were determined by X-ray crystallography

  合成了两个基于半乳糖衍生支架的过渡金属阳离子的新配体：1,5-脱水-2-脱氧-3,4,6-三-O-（2-吡啶甲基）-D-半乳糖醇和甲基2-脱氧-3,4,6-三-O-（2-吡啶甲基）-α-D-吡喃半乳糖苷。这些配体允许分离为Co（II）和Ni（II）配合物的单晶。两种配合物的结构均通过X射线晶体学测定，显示出包括糖结合的氧原子的配位球。发现在两种情况下，糖的配体都在复合物的晶体结构中具有高能构象。这些构象包含与糖结合的氧原子的排列，类似于在多元醇-金属和碳水化合物-金属络合物中观察到的排列。