p-cresyl 2-O-benzoyl-3,5-di-O-benzyl-1-thio-α-D-arabinofuranoside | 402758-78-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-cresyl 2-O-benzoyl-3,5-di-O-benzyl-1-thio-α-D-arabinofuranoside
• 英文别名: p-tolyl 2-O-benzoyl-3,5-di-O-benzyl-1-thio-α-D-arabinofuranoside；[(2R,3S,4R,5R)-2-(4-methylphenyl)sulfanyl-4-phenylmethoxy-5-(phenylmethoxymethyl)oxolan-3-yl] benzoate
• CAS: 402758-78-5
• 化学式: C₃₃H₃₂O₅S
• 分子量: 540.68
• InChiKey: PBACSNJUMXQVQX-RASQHNTCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  39
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  79.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  p-cresyl 2-O-benzoyl-3,5-di-O-benzyl-1-thio-α-D-arabinofuranoside 在 palladium on activated charcoal N-碘代丁二酰亚胺 、 molecular sieve 、 氢气 、 sodium methylate 、 silver trifluoromethanesulfonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 methyl 5-O-(α-D-arabinofuranosyl)-3-O-(2-O-(β-arabinofuranosyl)-α-D-arabinofuranosyl)-α-D-arabinofuranoside
  参考文献：
  名称：

  分枝杆菌的阿拉伯呋喃糖苷：高度分支的六糖及其相关片段的合成，其中包含β-阿拉伯呋喃糖基残基。

  摘要：

  报道了11种含有β-阿拉伯呋喃糖基残基的寡糖（4-14）的合成。聚糖是分枝杆菌细胞壁复合物中发现的两种多糖阿拉伯半乳聚糖和脂质阿拉伯糖甘露聚糖的全部片段。在制备靶标中，关键步骤是低温糖基化反应，该反应安装了具有良好至优异立体控制效果的β-阿拉伯呋喃糖基残基。

  DOI：

  10.1021/jo010910e
• 作为产物：
  描述：

  Methyl 2,3-anhydro-5-O-benzyl-α-D-lyxofuranoside 在 吡啶 、 sodium benzoate 、 三氟化硼乙醚 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 p-cresyl 2-O-benzoyl-3,5-di-O-benzyl-1-thio-α-D-arabinofuranoside
  参考文献：
  名称：

  糖苷键合成中的 2,3-脱水糖。含有α-和β-阿拉伯呋喃糖基键的寡糖的高度立体选择性合成

  摘要：

  由碳水化合物介导的生物学重要事件的不断发现引起了人们对寡糖合成和糖苷键形成新方法开发的极大兴趣。在本文中，我们报告了 2,3-脱水呋喃糖硫糖苷 (1, 5) 和糖基亚砜 (2, 6)，其中羟基 C-2 和 C-3 被“保护”为环氧化物，糖基化醇与极高的立体声控制度。与这种全新类型的糖基化剂反应的主要或唯一产物是其中新形成的糖苷键与环氧化物部分顺式。我们进一步证明，随后环氧化物部分的亲核打开在碱性条件下进行，以高产率和良好至极好的区域选择性得到产物。主要的开环产物具有阿拉伯立体化学，因此该方法构成了合成阿拉伯呋喃糖苷的新方法。在环...

  DOI：

  10.1021/ja029302m

文献信息

• Influence of Steric Crowding on Diastereoselective Arabinofuranosylations
  作者：Maidul Islam、Gaddamanugu Gayatri、Srinivas Hotha

  DOI：10.1021/acs.joc.5b00964

  日期：2015.8.21

  their significance in controlling disease spurred interest in developing strategies for their diastereoselective synthesis. Mtb uses enzymes to achieve diastereoselectivity through noncovalent interactions. Of the two possible glycosidic linkages, chemically, 1,2-trans linkage is relatively easy to synthesize by taking advantage of neighboring group participation, whereas synthesis of the 1,2-cis linkage

  结核分枝杆菌（Mtb）细胞表面上阿拉伯呋喃糖苷的出现及其在控制疾病中的意义激发了人们开发非对映选择性合成策略的兴趣。Mtb使用酶通过非共价相互作用实现非对映选择性。在两个可能的糖苷键中，化学上，1,2-反式键相对容易通过利用邻近基团的参与来合成，而1,2-顺式的合成链接非常困难。在本文中，用硫代吡啶基，亚氨酸酯和硫代甲苯基供体以及拥挤程度不同的糖基受体研究了立体化学对阿拉伯呋喃糖基化非对映选择性的影响。观察到受体的立体化学环境存在细微差异，从而改变了呋喃糖苷形成的非对映选择性。该努力的结果表明，可以通过在较低温度下在对空间要求高且反应性较低的底物上进行反应来方便地合成1，2-顺式阿拉伯呋喃糖苷。
• Characterization of a Distinct Arabinofuranosyltransferase in <i>Mycobacterium </i><i>smegmatis</i>
  作者：Jian Zhang、Kay-Hooi Khoo、Sz-Wei Wu、Delphi Chatterjee

  DOI：10.1021/ja070330k

  日期：2007.8.1

  The D-arabinans in Mycobacterium are essential, extraordinarily complex entity comprised of D-arabinofuranose residues which are rarely found in nature. Despite the well-recognized importance of the mycobacterial arabinan, delineation of the arabinosylation process has been severely hampered due to lack of positively identified arabinosyltransferases. Identification of genes involved in arabinan biosynthesis entailed the use of ethambutol (EMB), a first-line antituberculosis agent that is known to inhibit cell wall arabinan synthesis. The three genes (embA, embB, and embC) encode novel membrane proteins, implicated as the only known mycobacterial arabinosyltransferases to this date. We have now adapted a multifaceted approach involving development of convenient arabinosyltransferase assay using novel synthetic acceptors to identify arabinosyltransferase/s that will be distinct from the Emb proteins. In our present work, Mycobacterium smegmatis mc(2)155 (WTMsm) was used as a model to study the biosynthesis of cell wall arabinan. In an in vitro assay, we demonstrate that transfer of only alpha-Araf had occurred from decaprenylphosphoryl-D-arabinofuranose (DPA) on a newly synthesized branched acceptor [alpha-D-Araf](2)-3,5-alpha-D-Araf-(1 -> 5)-alpha-D-Araf-(1 -> 5)-alpha-D-Araf (1) with an octyl aglycon. Higher molecular weight (up to Ara(10)) oligomers were also detected in a parallel reaction using cold phosphoribosepyrophosphate (pRpp). Matrix-assisted laser desorption ionization time-of-flight tandem mass spectrometry (MALDI-TOF MS/MS) analysis of these products revealed that isomeric products were formed and initiation and elongation of arabinan can occur either on the 5-arm or 3-arm of the branched 3,5-alpha-D-Araf. Individual embA, embB, and embC knockout strains retained this alpha-1,5 arabinosyltransferase activity, and the activity was partially inhibited by ethambutol. This particular enzyme function is distinct from the function of the Emb proteins.
• Synthesis of Oligosaccharide Fragments of Mannosylated Lipoarabinomannan Appropriately Functionalized for Neoglycoconjugate Preparation
  作者：Rajendrakumar Reddy Gadikota、Christopher S. Callam、Ben J. Appelmelk、Todd L. Lowary

  DOI：10.1081/car-120021696

  日期：2003.1.6

  The synthesis of a panel of oligosaccharides that are fragments of mannosylated lipoarabinomannan from Mycobacterium tuberculosis is reported. The compounds were prepared as their 8-aminooctyl glycosides to enable their easy incorporation into neoglycoconjugates.
• 2,3-Anhydro Sugars in Glycoside Bond Synthesis. Highly Stereoselective Syntheses of Oligosaccharides Containing α- and β-Arabinofuranosyl Linkages
  作者：Rajendrakumar Reddy Gadikota、Christopher S. Callam、Timothy Wagner、Brian Del Fraino、Todd L. Lowary

  DOI：10.1021/ja029302m

  日期：2003.4.1

  biologically important events mediated by carbohydrates has generated great interest in the synthesis of oligosaccharides and the development of new methods for glycosidic bond formation. In this paper, we report that 2,3-anhydrofuranose thioglycosides (1, 5) and glycosyl sulfoxides (2, 6), in which the hydroxyl groups C-2 and C-3 are “protected” as an epoxide, glycosylate alcohols with an exceptionally

  由碳水化合物介导的生物学重要事件的不断发现引起了人们对寡糖合成和糖苷键形成新方法开发的极大兴趣。在本文中，我们报告了 2,3-脱水呋喃糖硫糖苷 (1, 5) 和糖基亚砜 (2, 6)，其中羟基 C-2 和 C-3 被“保护”为环氧化物，糖基化醇与极高的立体声控制度。与这种全新类型的糖基化剂反应的主要或唯一产物是其中新形成的糖苷键与环氧化物部分顺式。我们进一步证明，随后环氧化物部分的亲核打开在碱性条件下进行，以高产率和良好至极好的区域选择性得到产物。主要的开环产物具有阿拉伯立体化学，因此该方法构成了合成阿拉伯呋喃糖苷的新方法。在环...
• Arabinofuranosides from Mycobacteria:  Synthesis of a Highly Branched Hexasaccharide and Related Fragments Containing β-Arabinofuranosyl Residues
  作者：Haifeng Yin、Francis W. D'Souz、Todd L. Lowary

  DOI：10.1021/jo010910e

  日期：2002.2.1

  The synthesis of 11 oligosaccharides (4-14) containing beta-arabinofuranosyl residues is reported. The glycans are all fragments of two polysaccharides, arabinogalactan and lipoarabinomannan, which are found in the cell wall complex of mycobacteria. In the preparation of the targets, the key step was a low-temperature glycosylation reaction that installed the beta-arabinofuranosyl residues with good

  报道了11种含有β-阿拉伯呋喃糖基残基的寡糖（4-14）的合成。聚糖是分枝杆菌细胞壁复合物中发现的两种多糖阿拉伯半乳聚糖和脂质阿拉伯糖甘露聚糖的全部片段。在制备靶标中，关键步骤是低温糖基化反应，该反应安装了具有良好至优异立体控制效果的β-阿拉伯呋喃糖基残基。