p-tolyl 5-O-trityl-1-thio-β-D-xylofuranoside | 887747-58-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: p-tolyl 5-O-trityl-1-thio-β-D-xylofuranoside
• 英文别名: p-Tolyl 5-O-trityl-1-thio-beta-D-xylofuranoside；(2S,3R,4R,5R)-2-(4-methylphenyl)sulfanyl-5-(trityloxymethyl)oxolane-3,4-diol
• CAS: 887747-58-2
• 化学式: C₃₁H₃₀O₄S
• 分子量: 498.643
• InChiKey: VLRHAMPJFPQCDM-ATIZSFMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  84.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  p-tolyl 5-O-trityl-1-thio-β-D-xylofuranoside 在 silver trifluoromethanesulfonate 吡啶 、 N-碘代丁二酰亚胺 、 4 A molecular sieve 、 phosphorus pentoxide 、 sodium hydride 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 31.33h， 生成 methyl 5-O-toluenesulfonyl-2,3-di-O-benzyl-α-D-xylofuranoside
  参考文献：
  名称：

  The 5-Deoxy-5-methylthio-xylofuranose Residue in Mycobacterial Lipoarabinomannan. Absolute Stereochemistry, Linkage Position, Conformation, and Immunomodulatory Activity

  摘要：

  Mycobacteria produce a cell-surface glycoconjugate, lipoarabinomannan (LAM), which has been shown to be a potent modulator of the immune response that arises from infection by these organisms. Recently, LAM from the human pathogens Mycobacterium tuberculosis and M. kansasii has been shown to contain an unusual 5-deoxy-5-methylthio-xylofuranose (MTX) residue as well as its corresponding oxidized counterpart, 5-deoxy-5-methylsulfoxy-xylofuranose (MSX). To date, the absolute configuration of these residues and their linkage position to the polysaccharide are unknown, as is their biological role. Through the combined use of chemical synthesis and NMR spectroscopy, we have established that the MTX/MSX residues in these glycoconjugates are of the D-configuration and that they are linked alpha-(1-4) to a mannopyranose residue in the mannan portion of the glycan. Conformational analysis of the MTX/MSX residue using NMR spectroscopy showed differences in ring conformation and as well as in the rotamer populations about the C-4-C-5 bond, as compared to the parent compound, methyl alpha-D-xylofuranoside. Two of the synthesized disaccharides, 3 and 34, were tested in cytokine induction assays, and neither led to the production of TNF-alpha or IL-12p70. In contrast, both demonstrated modest inhibitory properties when these same cytokines were induced using a preparation of Interferon-gamma and Staphylococcus aureus Cowan strain (SAC/IFN-gamma). These latter observations suggest that this motif may play a role in the immune response arising from mycobacterial infection.

  DOI：

  10.1021/ja057373q
• 作为产物：
  描述：

  三苯基氯甲烷 、 p-tolyl 1-thio-β-D-xylofuranoside 在 4-二甲氨基吡啶 作用下， 以 吡啶 为溶剂， 反应 14.0h， 以91%的产率得到p-tolyl 5-O-trityl-1-thio-β-D-xylofuranoside
  参考文献：
  名称：

  IMMUNOMODULATORY SACCHARIDE COMPOUNDS

  摘要：

  包含糖分子和5-去氧-5-甲硫氧基-木糖呋喃糖（MTX）基团或5-去氧-5-甲基磺氧基-木糖呋喃糖（MSX）基团的化合物，以及在调节炎症和免疫反应方法中使用这些化合物。

  公开号：

  US20070219144A1

文献信息

• Stereocontrolled Synthesis of α-Xylofuranosides Using a Conformationally Restricted Donor
  作者：Li Zhang、Ke Shen、Hashem A. Taha、Todd L. Lowary

  DOI：10.1021/acs.joc.8b00410

  日期：2018.8.3

  the use of thioglycoside donors possessing a conformationally restricting xylylene protecting group. The method was shown to provide the desired targets in good to excellent yield and stereoselectivity. Computational investigations support the proposal that the protecting group locks the electrophilic intermediate in these reactions into a conformation that leads to the high selectivity. The power

  许多生物学上相关的糖缀合物都具有1，2-顺式呋喃糖苷键，这是一类糖苷键，要以高的立体选择性引入仍然很困难。在本文中，我们报告了通过使用具有构象限制二甲苯基保护基团的硫代糖苷供体来解决此类连接的一个家族，即α-木呋喃糖苷的方法。结果表明，该方法可提供所需目标，且收率和立体选择性均良好。计算研究支持以下提议：保护基团将这些反应中的亲电子中间体锁定为导致高选择性的构象。该方法的强大能力是通过合成lipoarabinomannan（一种来自分枝杆菌的免疫调节多糖）形成的复杂六糖基序来证明的。
• [EN] IMMUNOMODULATORY SACCHARIDE COMPOUNDS<br/>[FR] COMPOSES SACCHARIDES IMMUNOMODULATEURS
  申请人：UNIV ALBERTA

  公开号：WO2007109561A1

  公开（公告）日：2007-09-27

  [EN] Compounds comprising a saccharide molecule and a 5-deoxy-5-methylthio-xylofuranose (MTX) moiety or a 5-deoxy-5-methylsulfoxy-xylofuranose (MSX) moiety, and use of such compounds in methods for modulating inflammation and immune responses.
  [FR] L'invention concerne des composés contenant une molécule saccharide et une fraction 5-déoxy-5-méthylthio-xylofuranose (MTX) ou une fraction 5-déoxy-5-méthylsulfoxy-xylofuranose (MSX), ainsi que l'utilisation de ces composés dans des méthodes de modulation de l'inflammation et des réponses immunitaires.