p-tolyl 2,3,4-tri-O-benzoyl-1-thio-α-D-mannopyranoside | 1005398-12-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-tolyl 2,3,4-tri-O-benzoyl-1-thio-α-D-mannopyranoside
• 英文别名: [(2R,3R,4S,5S,6R)-4,5-dibenzoyloxy-2-(hydroxymethyl)-6-(4-methylphenyl)sulfanyloxan-3-yl] benzoate
• CAS: 1005398-12-8
• 化学式: C₃₄H₃₀O₈S
• 分子量: 598.673
• InChiKey: VGOJOKPAEVYVKR-MTXZWBDTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  43
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  134
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  p-tolyl 2,3,4-tri-O-benzoyl-1-thio-α-D-mannopyranoside 在 N-溴代丁二酰亚胺(NBS) 、 二乙胺基三氟化硫 、 silver perchlorate 、 tin(ll) chloride 作用下， 以 二氯甲烷 为溶剂， 生成 6-O-acetyl-2,3,4-tri-O-benzoyl-α-D-mannopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-α-D-mannopyranosyl fluoride
  参考文献：
  名称：

  Vaccine Compositions For Marburg Virus

  摘要：

  本发明提供了用于产生针对马尔堡病毒的免疫反应的方法和免疫原组合物。该免疫原组合物包括从马尔堡病毒株中获得的抗原，结合油酸三萜佐酸类佐剂。

  公开号：

  US20120136142A1
• 作为产物：
  描述：

  4-methylphenyl 2,3,4-tri-O-benzoyl-6-O-trityl-1-thio-α-D-mannopyranoside 在 三异丙基硅烷 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以85%的产率得到p-tolyl 2,3,4-tri-O-benzoyl-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  5（6）-羧基荧光素在微波辅助合成荧光标记的O-二甘露糖基化肽中的稳定性

  摘要：

  方法为高效，自动化和能够通过赖氨酸进一步伸长的5（6） -羧基荧光素标记的赖氨酸（DDE）-Gly-Wang树脂的微波辅助的Fmoc固相合成Ñ ε氨基被描述。O形dimannosylated肽掺入到应用Fmoc-该树脂[α- d -Man（OBZ）4 - （1→6）-α- d -Man（OBZ）3 α1-]丝氨酸-OH和PEG- [α- d -Man（OBz）4-（1→6）-α- d -Man（OBz）3证明了α1-]-OH的结构单元。对条件进行了优化，以实现几种羧基荧光素标记的二甘露糖基化肽的高效自动合成。已显示5（6）-羧基荧光素对用于糖肽合成的微波条件稳定。所描述的方法学为制备用于生物学评估的各种荧光标记的糖肽（特别是O-二甘露糖基化的肽）提供了强大而灵活的合成平台。 碳水化合物-糖肽-甘露糖基化氨基酸-糖基化-固相合成

  DOI：

  10.1055/s-0029-1216820

文献信息

• Concise assembly of linear α(1→6)-linked octamannan fluorescent probe
  作者：Mohammad S. Aqueel、Vibha Pathak、Ashish K. Pathak

  DOI：10.1016/j.tetlet.2008.09.164

  日期：2008.12

  Synthesis of a fluorescently labelled (dansylated) linear alpha(1-->6)-linked octamannan, using glycosyl fluoride donors and thioglycosyl acceptors is described. A selective and convergent two-stage activation progression was executed to construct di-, tetra and octa-mannosyl thioglycosides in three glycosylation steps with excellent yield. Further a 5-N,N-Dimethylaminonaphthalene-1-sulfonamidoethyl

  合成的荧光标记 (dansylated) 线性 alpha(1-->6)-链接八甘露聚糖，使用糖基氟供体和 thioglycosyl 受体进行描述。执行选择性和收敛的两阶段活化进程，以在三个糖基化步骤中以优异的产率构建二、四和八甘露糖基硫糖苷。此外，5-N,N-二甲基氨基萘-1-磺酰氨基乙基（丹磺酰基）与1-叠氮乙基八甘露糖硫糖苷偶联。耦合产品的全局脱保护提供了所需的丹磺酰化同源线性 alpha(1-->6)-链接八甘露聚糖。
• Mannopyranoside Glycolipids Inhibit Mycobacterial and Biofilm Growth and Potentiate Isoniazid Inhibition Activities in <i>M. smegmatis</i>
  作者：Avisek Mahapa、Gopal Ch Samanta、Krishnagopal Maiti、Dipankar Chatterji、Narayanaswamy Jayaraman

  DOI：10.1002/cbic.201900040

  日期：2019.8

  Lipomannan‐based synthetic glycolipids exhibit higher inhibition efficiencies to mycobacterial growth, in preference to biofilm inhibition. A two‐ and threefold increase in inhibition potency is observed if the antibiotic isoniazid is supplemented with synthetic lipomannan glycolipids, thereby reducing the concentration of antibiotic required to inhibit mycobacterial growth and biofilm phases.

  被糖阻碍：基于脂甘露聚糖的合成糖脂优先于生物膜抑制作用，表现出对分枝杆菌生长的更高抑制效率。如果在抗生素异烟肼中添加合成的脂质甘露聚糖糖脂，则抑制力会提高2到3倍，从而降低抑制分枝杆菌生长和生物膜阶段所需的抗生素浓度。
• Synthetic Arabinomannan Heptasaccharide Glycolipids Inhibit Biofilm Growth and Augment Isoniazid Effects in<i>Mycobacterium smegmatis</i>
  作者：Krishnagopal Maiti、Kirtimaan Syal、Dipankar Chatterji、Narayanaswamy Jayaraman

  DOI：10.1002/cbic.201700247

  日期：2017.10.5

  synergy: Non‐cytotoxic synthetic mannopyranosyl‐arabinofuranoside heptasaccharide glycolipids have been identified as potent dose‐dependent inhibitors of biofilms of M. smegmatis, with minimum biofilm growth inhibition concentrations (MBICs) of 100 μg mL−1. These glycolipids also synergistically augment the MBIC of isoniazid more than threefold, at 30 μg mL−1.

  药物协同作用：非细胞毒性的合成甘露吡喃糖基-阿拉伯呋喃糖苷七糖糖脂已被确定为耻垢分枝杆菌生物膜的强效剂量依赖性抑制剂，最小生物膜生长抑制浓度（MBIC）为100μgmL -1。这些糖脂还以30μgmL -1协同增效异烟肼的MBIC超过三倍。
• Oligomannan Synthesis Using Ionic Liquid Supported Glycosylation
  作者：Ashish K. Pathak、Charu K. Yerneni、Zac Young、Vibha Pathak

  DOI：10.1021/ol702743x

  日期：2008.1.1

  The synthesis of complex oligosaccharides has been a challenge for researchers. Herein, we describe a strategy for the synthesis of an activated oligomannan 1 that employs ionic liquid (IL) support glycosylation methodology on an IL-tagged mannosyl fluoride donor. This method is capable of rapidly producing linear alpha(1 -> 6) oligomannan thioglycosides in a convenient and cost-effective manner without the need of column purification after each glycosylation step.
• Concise synthesis of the tetrasaccharide repeating unit of the O-polysaccharide isolated from Edwardsiella tarda PCM 1156 strain
  作者：Rituparna Das、Mukul Mahanti、Balaram Mukhopadhyay

  DOI：10.1016/j.carres.2014.08.004

  日期：2014.11

  A convergent strategy has been developed for the synthesis of the tetrasaccharide repeating unit of the O-antigen from Edwardsiella tarda PCM 1156. Sequential glycosylations of a series of rationally protected monosaccharide intermediates were achieved either by the activation of thioglycosides using N-iodosuccinimide (NIS) in conjunction with H2SO4-silica or by activation of trichloroacetimidate by H2SO4-silica only. All glycosylation reactions resulted in the formation of the desired linkage with absolute stereoselectivity and yielded the required derivatives in good to excellent yields. Both azido and phthalimido groups have been used as the precursor of the desired acetamido group depending on the requirement of 1,2-cis- or 1,2-trans-glycosidic linkage. (C) 2014 Elsevier Ltd. All rights reserved.