2,3,5,6-tetra-O-benzyl-D-galactofuranose

• 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: 2,3,5,6-tetra-O-benzyl-D-galactofuranose
• 英文别名: 2,3,5,6-tetra-O-benzyl-α/β-D-galactofuranose；(3R,4S,5S)-5-[(1R)-1,2-bis(phenylmethoxy)ethyl]-3,4-bis(phenylmethoxy)oxolan-2-ol
• 化学式: C₃₄H₃₆O₆
• 分子量: 540.656
• InChiKey: ZMABYDSAYWDZLA-BJPULKCASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  40
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,3,5,6-tetra-O-benzyl-D-galactofuranose 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 以70%的产率得到2,3,5,6-tetra-O-benzyl-D-galactono-1,4-lactone
  参考文献：
  名称：

  被设计为三种分枝杆菌半乳糖呋喃糖加工酶抑制剂的前所未有的磺酰化膦外糖的合成。

  摘要：

  这项研究报告了一种合成砜和膦酸酯的外糖的新方法。这种合成策略提供了一种生成具有两个吸电子基团的外糖的方法，并应用于呋喃糖和吡喃糖系列中的八种不同的碳水化合物。这些四取代的烯醇醚的Z / E构型可以使用NMR光谱技术确定。的脱保护，外切-glycal后跟UMP（尿苷酸）耦合产生的两个新的UDP（尿苷二磷酸）-galactofuranose类似物。这两个ž / é异构体被评价为UGM，GL的抑制剂˚FT1和Gl f T2，这是三种分枝杆菌半乳糖呋喃糖加工酶。分子46-（E）是迄今为止报道的第一个特征性的Gl f T1抑制剂，并且还发现它以可逆方式有效抑制UGM。有趣的是，胃肠˚F T2显示出对（更好的亲和力Ž）异构体。在本工作中研究的这三种酶不仅很有趣，因为从机械上讲它们仍然是深入研究的主题，而且因为它们构成了开发新型抗分枝杆菌剂的非常重要的目标。

  DOI：

  10.1002/chem.201603161
• 作为产物：
  描述：

  methyl-β-D-galactofuranoside 在 硫酸 、 sodium hydride 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 2,3,5,6-tetra-O-benzyl-D-galactofuranose
  参考文献：
  名称：

  d-Galactofuranosylphosphonates. First Synthesis of UDP-C-d-galactofuranose

  摘要：

  The chemical synthesis of two phosphono analogues of D-galactofuranosyl phosphate was performed. The natural phosphate seemed to be too labile to allow the chemical synthesis of UDP-Galf, these C-galactofuranosides are stable pharmacophores, and the cr-phosphono analogue has been easily converted into UDP-C-Galf. UDP-C-Galf was tested as a competitive inhibitor of UDP-galactopyranose mutase and showed inhibition of Galf formation. Thus, it is of potential interest as an antimycobacterial agent; as an active molecule against Trypanosoma cruzi, the causative agent of South American trypanosomiasis (Chagas' disease), and as a stable analogue for use in UDP-galactopyranose mutase crystallization studies.

  DOI：

  10.1021/jo990196p

文献信息

• Synthesis of α-d-Galf-(1→2)-d-galactitol and α-d-Galf-(1→2)[β-d-Galf-(1→3)]-d-galactitol, oligosaccharide derivatives from Bacteroides cellulosolvens glycoproteins
  作者：Lucía Gandolfi-Donadío、Gabriel Gola、Rosa M. de Lederkremer、Carola Gallo-Rodriguez

  DOI：10.1016/j.carres.2006.07.013

  日期：2006.11

  Abstract The synthesis of α- d -galactofuranosyl-(1→2)- d -galactitol, which has been isolated by reductive β-elimination from glycoproteins of Bacteroides cellulosolvens and Clostridium thermocellum , is described. The approach of selective glycosylation of an aldono-1,4-lactone by the trichloroacetimidate method was employed. The synthesis of α- d -Gal f -(1→2)[β- d -Gal f -(1→3)]- d -Galol, that

  摘要描述了通过还原性β-消除从拟杆菌细菌和热纤梭菌的糖蛋白中分离得到的α-d-半呋喃呋喃糖基-（1→2）-d-半乳糖醇的合成方法。采用了通过三氯乙亚氨酸酯方法选择性糖基化1，4-内酯的方法。还报道了α-d-Gal f-（1→2）[β-d-Gal f-（1→3）]-d -Galol的合成，其在两个端基异构构型中均包含Gal f单元。这些是最早在天然产物中发现的具有α-d -Gal f的合成寡糖。
• Design, synthesis and bioactivity evaluation of Galf mimics as antitubercular agents
  作者：Chunyan Liu、Linyu Hou、Aiguo Meng、Gang Han、Weiguo Zhang、Shende Jiang

  DOI：10.1016/j.carres.2015.11.002

  日期：2016.6

  (13)C NMR, mass spectral and element analysis. All the newly prepared compounds were screened for their antitubercular activities. Bioactivity assays manifested that most of Galf mimics exhibited good antitubercular activities. Especially compound 4d and 4e displayed remarkable antitubercular efficacies, which were comparable to ethambutol.

  合成了一系列新颖的Galf模拟物，并通过IR，（1）H NMR，（13）C NMR，质谱和元素分析对其进行了表征。筛选所有新制备的化合物的抗结核活性。生物活性测定表明，大多数Galf模仿物表现出良好的抗结核活性。特别是化合物4d和4e表现出显着的抗结核功效，与乙胺丁醇相当。
• Convergent Synthesis of Oligosaccharide Fragments Corresponding to the Cell Wall <i>O</i> -Polysaccharide of <i>Salmonella enterica</i> O53
  作者：Debashis Dhara、Anup Kumar Misra

  DOI：10.1002/open.201500102

  日期：2015.12

  oligosaccharides. The development of synthetic strategies to prepare glycoconjugate derivatives against pathogenic bacterial strains is therefore of great interest. Oligosaccharide fragments corresponding to the repeat unit of the cell wall O‐antigen of Salmonella enterica strain O53 were synthesized in good yield. Sequential and block glycosylation strategies were used for the synthesis of the target compounds

  常规的糖缀合物疫苗是使用从细菌发酵中分离的多糖制备的，这种方法具有一些重大缺陷，例如处理活细菌菌株，存在生物杂质以及寡糖表位结构的批间差异。但是，在许多情况下，已经显示出与蛋白质缀合的适当结构的合成片段可能是一种有效的疫苗，可以规避使用全长寡糖的缺点。因此，制备针对病原性细菌菌株的糖缀合物衍生物的合成策略的发展引起了极大的兴趣。对应于肠沙门氏菌细胞壁O抗原重复单元的寡糖片段以高产率合成了O53菌株。顺序和嵌段糖基化策略用于目标化合物的合成。在合成策略中使用了许多最新开发的反应条件。还针对多个糖基化步骤开发了一个单锅反应方案。所有糖基化反应的立体选择性结果都非常好。
• Novel glycolipid TLR2 ligands of the type Pam2Cys-α-Gal: Synthesis and biological properties
  作者：Jean-Sébastien Thomann、Fanny Monneaux、Gaëlle Creusat、Maria Vittoria Spanedda、Béatrice Heurtault、Chloé Habermacher、Francis Schuber、Line Bourel-Bonnet、Benoît Frisch

  DOI：10.1016/j.ejmech.2012.02.039

  日期：2012.5

  A more complete understanding of the mechanism of action of TLR agonists has fueled the investigation of new synthetic immunoadjuvants. In this context, we designed and synthesized glycolipids of the type Pam(2)Cys-alpha-Galactose as novel immunoadjuvants. Their synthesis required modifying a hydrophobic tBoc-[2,3-bispalmitoyloxy-(2R)-propyl]-R-cysteinyl moiety, i.e. the minimal structure required for TLR2 agonist activity, by addition of a hydrophilic head, either an alpha-Galactosylpyranose or an alpha-Galactosylfuranose to gain respectively Pam(2)CGalp and Pam(2)CGalf. While preparing a carbohydrate building block, an unexpected stereoselectivity was observed during a halide ion-catalytic process on a protected galactofuranose: the alpha anomer was obtained with surprisingly high selectivity (alpha/beta ratio > 9) and with good isolated yield (51%). The TLR2 binding properties of Pam(2)CGalp and Pam(2)CGalf were then fully evaluated. Their efficiency in triggering the proliferation of BALB/c mouse splenocytes was also compared to that of Pam(2)CAG and Pam(3)CAG, two well-established ligands of TLRs. Moreover, the maturation state of murine dendritic cells previously incubated with either Pam(2)CGalp or Pam(2)CGalf was monitored by flow cytometry and compared to that induced by lipopolysaccharide. Pam(2)CGalp and Pam(2)CGalf were found to be equivalent TLR2 agonists, and induced splenocyte proliferation and DC maturation. With very similar activity, Pam(2)CGalp and Pam(2)CGalf were also 10-fold to 100-fold better than Pam(2)CAG and Pam(3)CAG at inducing B cell proliferation. This represents the first time a glucidic head has been added to the tBoc-[2,3-bispalmitoyloxy-(2R)-propyl]-R-cysteinyl moiety whilst maintaining the immunomodulating activity. This should greatly enrich the data available on Pam(2)C structure/activity relationships. (C) 2012 Elsevier Masson SAS. All rights reserved.
• Synthesis of C-glycosyl compounds by the wittig iodocyclization procedure. Differences from mercuriocyclization
  作者：Francesco Nicotra、Luigi Panza、Fiamma Ronchetti、Giovanni Russo、Lucio Toma

  DOI：10.1016/s0008-6215(00)90878-4

  日期：1987.12